Screen Shot 2015-06-22 at 11.10.22 PM“My boyfriend never had any hesitations about being together: He wanted to be with me, live with me, marry me. For years.

One day, I come home to find that all his stuff is gone. He says he’s “confused” and isn’t sure if he loves me anymore. He says he met someone else. He takes down our Facebook pics, and puts her up instead. Then, he starts blowing up my phone, wants to hang out, so I say ok, and then he’s distant again. He tells me I’m his safety net. I know I’m a better fit for him—better looking, his age, with a good job and my own apartment. What gives?”


Oh boy.

This is the rock we beat ourselves against, over and over: We think that we know what’s “better” for the person we love and want, and decide our life should be dedicated to proving this fact, or at the very least, suffer endless indignation over it. I have done this many times over myself. Fruitlessly.

Let’s get this out of the way right now: It’s not about looks. Or income. Or your apartment. And what he thought or felt back then has little to do with what he does now, because we live in the present, which has been known to change. You say he never questioned his commitment to you…until he did (though did you ever think your hesitation may have played a role?). We don’t know that what he felt then was real and now is a mistake. He might have just bulldozed his way in because he wanted to. And is backing out now because he feels like it.

It’s not fair. It’s not fun. It may not even be logical. But none of that matters.

Because here’s the thing: relationships are not a logical puzzle that you solve by being the answer or getting it “right.” And the idea that being the rational choice assumes that relationships are rational, intellectual decisions. Hardly.

They are emotional, and based on how we feel, or think we feel, right now, rather than what looks good on paper (and those who go that route aren’t any happier). You may choose to ignore or repress them. Or you may choose to follow them, much to the dismay of everyone else involved.

It can be frustrating, maddening even, when someone you love willingly chooses someone you think is “all wrong” for him (or her, bear with me with pronouns here). Ask any first wife. How many beautiful, smart, capable women have watched partners cheat or leave altogether with women who are younger, dumber, broke, 20 pounds heavier, a smoker.

Good looks, a sense of humor, a string of accomplishments, and a killer bank account are not a vaccine for loss (see: Anyone with even one of those things). And the sooner you realize that, the better.

Men leave women who love them for women who don’t, or women who treat them badly, or women who just suck. And vice versa. Even when it’s deemed wrong or unethical. (Do I have to take you back to Hugh Grant and Divine Brown?)

And that’s why to assume that it’s you, or something you could have done differently, is not the answer, and it’s certainly not helpful—except that, more often than not, it helps YOU because it allows you to decide he’s stupid, wrong, making a mistake. He may be! But he’s making it anyway.

Stop wondering why he so clearly isn’t choosing the “right” fit for him. Because you’re missing the most important part of this picture: Since when was this all about how you fit his life? Don’t you also want someone who fits into yours? Because he doesn’t fit. He walked away.

I can’t read his mind and I don’t know you, Alice. But I know that if you have to build a case for why he should be with you, no case will ever be enough.

I once had a boyfriend who was 100% not a fit for me. At the time, he was earning his MBA from Harvard, and fancied himself a bit of a brainiac. And he was smart. The day I went over to end it, because the whole thing was making me nutty and not in a good way, he talked me out of it. He said, and I quote, I didn’t have a good enough “argument” for breaking up with him.

I was dumbfounded. I didn’t have an argument. I just started to cry. He attempted to intellectually bully his way out of a breakup! I’d never seen anything like it, before or since. It ended not long after.

So do yourself a favor and stop trying to rationalize why he should choose you and acting as if the court should rule in your favor because he has mistreated you. Besides, what do you win? Him? You don’t want him, trust me.

At some point, you have to take ownership of your role here. If someone can’t make you feel inferior without your consent, then no one can make you their safety blanket unless you continue to act like one.

*Alice is not her real name. I paraphrased her very long letter, and disguised the details a bit because she really does not want him to know. Obviously.

Having some dating issues or feeling stuck? I hear you. Truly I do. Use this link to get 25% off my online course, Stop Hating, Start Dating – I will change the way you think about and approach this whole thing. 

I've heard of shy, but this is nuts.

I’ve heard of shy, but this is nuts.

I like to occasionally check out the West Side Rag, this local blog listing all the restaurant openings and closings and health code violations and weird crimes that happen on the Upper West Side. And I saw this story, about a woman who had a crush on a neighborhood guy when she was 19 years old and new to New York City. She thought he was so hot. She dubbed him “Teen Idol.”

And then she did not a damn thing about it for 20 years.

That’s right. The occasion for the story isn’t just that this woman stalked him all over town, but that she wistfully watched him from afar, living his life, until one day, like a year ago, she spotted him in a building where he was working, and where she would be coming regularly. So, you know, she finally got up the nerve to introduce herself. Two decades later.

And just the other day, they got married in Central Park. That’s great! It’s also a crying shame.

Seriously?! Maybe the journalist took some liberties; maybe the woman thought he was cute but wasn’t that interested. Maybe she was involved with someone else 15 of the past 20 years. The story doesn’t say.

But what I do now is this—she waited until she was 39 to grow a pair. OK, so maybe she might have made a move when she was 22, and he may not have been ready for her, or ok, they could have gotten together, had a hot thing going, and flamed out before either of them hit 30. Doesn’t matter. You can call it fate, but I call it crazy.

My problem has always been that people say, “Ah if it’s meant to be, it will be.” But I couldn’t disagree more, because that’s like playing a chess game with fate and deciding that in order to win you won’t move any of your pieces around.

(Read more of my strong feelings about fate. Strong language advisory.)

Say something! 

My question to you is this: You see someone who appeals to you, even a little? What on God’s earth are you waiting for? This city, and most cities, are crawling with people, and the continual churn of randomness of it all is such that you just may not get this chance again.

You say, “Oh but I don’t want to have to ask a guy out.” (Men, you have no excuse. Man up.) But ladies, you don’t have to do that. But you do have to swing that door open so he knows you’re there and that he’s welcome to walk through. And I can’t tell you how many times it’s paid off (many). Including my last serious relationship, which happened because I left my card behind and he followed up.

Ok, I’ll admit, even I choke sometimes: I was playing touch football in a Zogsports league as I do in the spring and fall, and I spotted a cutie, but was like, Jesus, what the hell do I do? Walk up to him at 3pm on a Sunday and ask him out? That’s weird. Hit on him in front of his friends as they change their shoes? No. So I didn’t do anything. Like a dummy.

Then…last game of the season, guess who we’re playing. Yup. It was a tense game, overtime, the whole thing. We win. Long story, I was late, so I hadn’t played this game, but you better believe I jumped in to do the whole “good game” hand shake thing. And when I got to this handsome fella, I shook his hand and smiled and said quite simply, “You’re so cute.” I said it with a big smile and a silly energy, since it was a high-energy game and I just went with it. “You’re cute, too,” he said. “Well, I regretted not telling you that the first time we played you,” I said.

His reply? “Want to get a drink sometime?”

Yes. Yes I would.

Truth is, he could have said, “Oh, that’s sweet, but I’m married,” or “Why thank you,” and then nothing. Who cares? What do I lose by doing that? Nothing. How am I supposed to know what his deal is. It’s the most blissfully ignorant moment of all. Worst case scenario? He is blushing and flattered and you made his damn day.

Bottom line: Do not wait around and stare at people from afar. Make yourself known. Or you’ll find yourself hobbling toward some old hottie in the nursing home, saying, Didn’t you used to eat at Ray’s Pizza in the 90s? And then your dentures will fall out of your head.

(Read also: How to happen to the hottest guy in the room.)

subway - mediumLove can happen pretty much anywhere. And your local public transportation system is teeming with love-hungry folks. The train (or subway, or bus, whatever) is a cocktail that’s being shaken around the clock: You never know whom you’ll end up next to or when.

And since you may find yourself on the subway at one point or another, there’s no reason you can’t make a connection there. You don’t need a bartender in range to connect with another single person. So, here are my tips for meeting someone on line—the MTA line, that is.

1. Get within 5 feet of that person. Obviously, you’re not going to yell across a car, especially a crowded one. Work your way into that person’s vicinity, but do it nonchalantly, as opposed to making a beeline, which can come off as aggressive.

2. Make eye contact. Now, granted if this person is staring at their phone, staring them down won’t work and will come off creepy if and when he or she happens to look up. If you DO make eye contact, don’t hold it like a crazy person, but smile and hold their gaze for an extra beat, then look away (this is, of course, Flirting 101). SMILE IS KEY—it registers a connection right away. It says, “I have noticed you.”

3. Initiate a conversation. This is key if there really is no way to make eye contact because s/he’s staring at his phone. And don’t delay. Time on a train is limited, and he who hesitates is lost. The longer you wait, the more likely you are to lose your nerve. Resist the urge to script your conversation preliminarily, because that’ll create more mental obstacles. Just start it, and let it go where it goes.

Now, the initiation has to feel natural to you. And so I offer you a few options, and what feels most natural to you will depend on your personality type. The idea that you “can’t” start a convo b/c: you’re introverted, shy, a girl—all that is garbage. You don’t need to be some alpha dude to start a harmless convo.

a) The question. This is the most harmless way to break through the stranger-veneer is to simply ask something. You don’t have to pretend to be a tourist (bad idea to lie) to ask a simple question (I do it all the time, for reals). “Hey, do you know if this goes to Wall Street” or “Do you live in this area? Would you happen to know if…” fill in the blank.

This serves two purposes: one, it breaks thru the silence and establishes contact, but it also puts the other person in the position of confidence and power because you are asking for their help. Trust me, this is key. I’ve had people ask me as I’m reading my Kindle, “So, what do you think of that Kindle?” and I am happy to talk about it.

b) The compliment. Flattery will get you everywhere, or at least, most places. It’s true. The hottest girl and even the most styling dude can’t get enough of them, nor can the rest of us. But there’s a right and wrong way, and there is a gender breakdown.


Cute girls will be on guard, because they know that compliments, while nice, can raise a flag and we wonder “What does he want?” So avoid anything that makes them feel put on the spot in a weird way, like “You have such beautiful eyes” or the like. Don’t make it sound like a line. Give a genuine compliment and give it with no strings attached. I’ve heard women say they don’t like when someone compliments a THING they have/own (“Who makes those cool shoes”) because then it’s more about the item than, well us. But I still think it’s ok, as long as it’s a genuine compliment, and I’m in there somewhere (“Cool shoes. They look great on you.”)


Men don’t get complimented all that much (maybe ever, especially by strangers), and they want them as much as anyone. So you kinda can’t go wrong here. A genuine, friendly compliment on just about anything will open a guy right up. In this case, I DO think complimenting a guy on what he is wearing/has is key because it not only says you noticed, but confirms his good taste. Ladies, you have it easy.

I will underscore this next point: DO NOT give a weirdo pickup line. I shouldn’t even have to say that. For this to work, it has to sound like genuine, spontaneous conversation.

c) The shared moment. Crazy stuff happens on the train. When it does, I consider it a gift from the subway gods. Use it. A mariachi band comes on at 8:30am in full regalia. A crazy person starts singing opera on the L. A couple starts yelling at each other. Who knows. If it happens, it’s a great opportunity to connect with this person in a way that is memorable, because it’s something you experienced together.

This is where humor really comes into play, and if you happen to be funny, witty, or observant in any way, this is the time to strike. You can make eye contact, roll your eyes, and say something like, “Man, I can’t stand mariachi in the morning. I prefer it on an evening train, during happy hour, don’t you?” You don’t have to be Louis CK to make someone laugh to get a response. It’s often a great tension breaker, and people get nervous on the train.

4. Move the conversation along. You established contact. Great! Now, move past whatever sparked the convo (the Kindle, the great shoes, etc) to real conversation. Unless all you really wanted was a consumer review of e-readers, and I doubt that. Nor is it really a shoe conversation. You want to see if you could connect with this person in a real way. Here’s where you can say something like, “You look familiar. I’m sure I’ve seen you on this train before. Do you work downtown? Yeah? What do you do?” And you’re off to the races.

5. Get a name, a number, website, a Twitter handle, anything. Remember, the goal here is not to have restaurant reservations or know her life story before you reach 72nd street, but to establish some kind of connection so that you can be in touch once you part ways. That and that alone is the goal of an en route meet-cute.

Ladies, you can do this as well as a guy can. You can say lots of things besides, “Can I get your number,” which for some reason, I’ve never liked. It sounds like you’re asking for a handout, unearned. The key is to make sure that person knows you’re interested in him or her. You must take the risk here and let someone know you’re interested in THEM, and while I know that’s the most terrifying part, all of this is worth nothing if you don’t do it.

Some options:

“I’d love to see you more than just by accident. Want to get coffee sometime?” or “Well, look, you seem really cool and I’d love to see you again, but on purpose. Can we stay in touch?” See? Harmless. Men, I’d offer your card if you have one but also get her info (whichever way she prefers—email, text, Twitter, whatever). You can take a moment to key each other’s info into your phones, but the problem is if you forget that person’s name, good luck finding it. Again, time is of the essence.

Ladies: I see no harm at all in offering a card—a biz card is fine, but it’s not a bad idea to have basic contact or ‘calling’ cards as they used to be called that has the info you want to share on them. Bottom line here, if you feel weird asking a guy for his number, etc, I like offering a card and saying, “Email me if you’d like to get together sometime.” I’ve done it many times to strangers I’ve met—some called, others didn’t. No harm, no foul. One did. That was all that mattered.

(Check out more advice on subway meet-cutes in this story on dnainfo.)

Who’ll run this mother? Girls. And shit will blow up along the way. (click to watch Beyonce at her finest)

Feminism has done a lot of good—for you, me, all the women you know and don’t know. I’m all about girl power, and go women. Yes.

But there’s one area where feminism has not served me well.  And that is dating. Why? Because, having been raised in the 80s, I came of age with the strong impression that men were basically up to no good. In the movies, TV shows, general cultural messages, men were by and large aggressive, incorrigible boors. They could hurt you. At the very least, they might get in your way. The good news was you probably didn’t need them.

Men Not Required

This was easy for me to believe because I went to an all-girls’ private and progressive catholic high school. Training grounds for the “men not required” mentality. I wore a uniform, no makeup, and had not an ounce of concern for boys, as they were not on my radar, and not deemed central to my life in any real way. Sure, we talked about them, but they were more like attractions than people I had relationships with. Beings I’d ogle and wonder at from the stands of a high school football game or at a dance. They were infrequent visitors in my life and I was a tourist in theirs.

I’d heard about how girls were cowed by the boys in public schools. Girls who didn’t get a shot at leadership, or acted dumb. I felt bad for them. I was certainly better off. For instance, we never mooned about waiting for someone to ask us to a school dance because when our school hosted one, it was on us to do the inviting. Every day was Sadie Hawkins day. We were running the place. And we would run the world.

As students of Oak Knoll High School, we weren’t just students. We were “women of promise.” We were the promise of a better future. I took this as a promise not to let anything, or anyone, get in my way.

During our senior year, we were shown some horrible video about how to avoid being the unfortunate drunk girl who gets date raped at a frat party. Stay sober, stay smart, and if someone goes to rape you, run for ze hills, screaming your head off.

That was my prep for dealing with men.

I got the impression that I could, should, and would run circles around guys. I’d be smarter, stronger, and savvier. And I was sure as shit not going to let any of them hurt me. Probably a good idea not to let any even get near me.

I’m Embarrassed This Happened

And guess what? I succeeded. I sneered at, and even humiliated men as a teenager, and if a guy liked me, I fairly resented him for it. At 14, I had what might be considered my first boyfriend. I’d met him at a spelling bee (not kidding). After two daytime dates held within earshot of parental supervision, I invited him to a dance at the boys’ school.

That night, I had a change of heart. Or rather, I panicked. As I saw him lean cautiously through the auditorium door in the flickering disco light (skinny kid, blond crew cut, windbreaker), I felt my heart ball up in a fist, and thought, No, no this was a mistake.

So, I ignored him. I returned to the safety of my friends and we watched him amble from one poorly lit corner of the room to the other, looking for me. I passed him once, and waved hi–and kept walking. I felt bad, but the way I see it now, not bad enough.

I left this boy stranded at a school dance where he knew no one but me. I am not proud of this. It remains one of the cruelest things I’ve ever done. I went home that night and said nothing–until the phone rang at 11:30 (which in the days of one-family land lines, was a big deal), and it was him. He was shocked and furious–as he should be. I had nothing to say–I shut down. I had no defense. When my mother got wind of what happened, she said, “What is wrong with you? How could you do that?” And I had no answer. I felt tough, and cold.

Then the letters started–scrawled black ink on both sides of thin looseleaf, declarations of love and war, and even threatened suicide, which scared me, even if I knew they likely weren’t true. I resented his neediness, his melodrama. I ignored him until he went away.

(I’ve since google stalked him and was happy to find that he was working as a computer technician in San Jose. I’m sure he never thinks of it–at least I hope he doesn’t.)

I can’t blame feminism for my piss-poor behavior of course, which I chalk up to fear, insecurity, and anything else that rules the mind and emotions of a 14-year-old girl. But it was reinforced by the notion that men were something to be dealt with, but not at all necessary or required.

…And Why This Became a Problem

Flash forward to adulthood and you can imagine how this might set me up with a bit of a handicap. Little did I know the inability to accept anything from a man, including love, would become a bigger problem. I guarded my virginity jealously, well into college, up until the bitter end, in fact. Because it meant I’d have to “lose” it—to someone who would take it from me. This is the worst metaphor ever–that’s what we need to lose!

I’ve come a long, long way since the ensuing years of tense serial monogamy in my 20s, and have far to go. I recognize that I have been angry and defensive for a big chunk of my life, and I’m not even sure why.

I Don’t Need You—Don’t You Love That?

I believe the flawed thinking that set my wheels in motion was believing that to want a man equalled neediness. No one likes needy. Even my uncle, a catholic priest, and my biggest fan in the world before he passed, said, “Terri, don’t be a desperate woman.” And so I figured if needed nothing especially from a man, I’d win. I just didn’t realize the cost of winning. And no, men do not love this! Who doesn’t want to be needed in some way?

I certainly don’t regret how feminism has served me: I’ve learned to be aggressive, tough, resilient, and have had many successes in my life as a result. I never have let a man get in my way–are you kidding? No one ever stood a chance. But now I’m trying to unlearn some of that–to learn what it means to soften, not weaken, and to expand, not constrict. To have power without the shiny, hard outer shell. This is incredibly fucking hard.

This may be the cost of post-feminist fallout. And you know, if that’s the price to pay for the incredible strides, I’ll take it. I’m also recognizing that I swung really hard in one direction and am gradually finding my way back to a more balanced state. My understanding of feminism has evolved, too–in that you don’t have to hate men or beat them in order to be a powerful woman.

Make no mistake–I wouldn’t undo feminism. And I have no regrets about the choices I’ve made in my life (except, of course, for the school dance episode, and a few others to be sure). But I’m well aware that my tendency to fight and compete and fear losing to men has made it incredibly hard for me to love the way I know I could. Even though marriage has never been a goal for me, how silly to think that you can–or should–get through life without loving, as often and as intensely as you can.

Of course, love requires all the things that scare me most: vulnerability, need, want, rejection. It’s hard for me to turn down a challenge–but I’m facing an entirely new one now. Because the softening and revealing and opening up that love requires is the very thing I’ve been steeling myself against. And I’m discovering that to win at not wanting, and not having, may not be a game worth winning, in the end.

Swipe left.

Swipe left.

I’ve recently re-entered the online dating pool, and surprise surprise, it’s just as much a hot mess as it was last time I was here. The bare torsos, the cringeworthy cliches, the fevered search for the next quick hookup.

But something has changed. The process has gone from a desktop portal of long-winded applications and essay contests to something far more visual and visceral. In other words, something more akin to how humans date. Less of a slog, too, and a whole lot more fun. Outside of the meet-someone-at-your-friend’s-bbq option, online dating has become more human than you think. And if you’re not doing it, as far as I’m concerned, you’re not really in the game.

We all have Tindr to thank (and Grindr before that) for disrupting the old college app-slash-memoir model, and making online dating feel faster, sexier, and more fun. Yes it’s a game. But you already knew that. It’s a handheld adventure, characterized by quick glances and physical gestures (the most important being the almighty swipe).

Now everyone’s doing it—you’ll find swipe functionality on OkCupid, Hinge, even Match, the old granddaddy of online dating. And don’t forget Cheek’d, which has also gotten some attention lately. After Lori Cheek, its founder, got chewed up on Shark Tank, she emerged with a new heat-seeking missile app which leverages the power of the virtual in the real world, letting you find other single people whom you may be missing on your daily commute or anywhere else. (Check out my interview with Lori on my show, Solopreneur.)

Rather listen than read? Done.

Guess which one's me!

Guess which one’s me!

It’s Like a Little Vegas You Hold In Your Hand

Your phone is now the portal to your love life, part mission control and part slot machine, complete with colors, movement,and flashing lights. But you have little to lose, and it’s hard not to get hooked. And you don’t even have to be dating to have fun doing it. I know more than a few happily married people who serve as Tindr proxies, swiping on behalf of their single friends. They want to help their friends find someone, sure, but they also want to play.

Some daters decry this shift in online dating gamification, saying that this doesn’t give them a chance to make their case, that this makes dating all about looks and nothing else. I have to remind them that we are human animals first, we’ve always looked and responded from a gut level, for millions of years before we wondered how people looked on paper. Sure, maybe you change your mind or someone wears you down. It happens. But I trust the gut check, always have. By the way, when in the history of human coupling has anyone met via a complicated admission process, complete with test scores and extra curriculars? I’ll tell you when: Arranged marriages, and you wouldn’t have been the one screening applications.



Partnering isn’t an executive function, not at first anyway. (See: Anytime someone looked great on paper but not in person. See also, anyone who swears they fell in love at first sight.) It’s not that people have gotten more superficial in dating–I don’t even know how that’s possible. So if you’re telling yourself this story, stop.

Don’t Be an Ass Swipe

What that means is that yes, pictures do matter, and I don’t mean you have to be a beauty queen or prom king, but you must show what you look like now, and not when you’re wearing a complete head-to-toe diver suit or dressed up as Lady Gaga. Getting a butt-first shot of you belaying down a mountain is not ideal, nor is a profile picture of you and several friends–because while you know which one you are, we don’t. Because when we finally do the task of flipping through your photos to find the common denominator, you don’t want us to be disappointed that you aren’t your hot cousin.

If you’re a dude, we don’t need to see pictures of you with a beautiful lady–sure, it may be your sister, but it could also be your ex. Maybe subconsciously you want to show your cred (look at what I got, or at least had). But while that works at parties, for some reason, it doesn’t play in pictures.

Don't you want to date me?  I'm available, like all these chairs.

Don’t you want to date me? I’m available, like all these chairs.

An anthropologist could have a field day studying men’s online dating pictures. I already do. But it goes without saying–if you want more right-swipes, avoid at all costs the bare torso, the blurred bathroom selfie, or you holding any kind of weapon. Skip the the landscape postcards, the still life. Keep that on your Instagram feed. And realize that what you think looks cool (you in your shades looking somewhere in the distance, often comes off as cold, intimidating, or a straight-up turn-off. Instead, try the one thing that so few guys do: Smile. Right into the camera. A real smile: eyes crinkled, teeth showing, you at your warmest and most real. That’s enough to give a thumb pause, and make us think you’re someone we’d like to meet.

I prob won’t text you back b/c I’m so cool and busy making deals by the water!

Ask it and you're not bringing sexy back.

Ask it and you’re not bringing sexy back.

Please, for the love of all things holy, stop asking the people you meet online if they’ve “had any luck” on the site. Stop, stop, stop.

I realize that you think it’s just in the spirit of fair gamesmanship (“hey we’re all on this together,” and “I’m such a good sport about this”) but you might as well sip your pinot grigio and ask, “So, who else are you currently fucking? How’s that going?”

I am convinced it starts innocently enough: a little conversational wind-up, some basic throat-clearing before you plow on to more interesting topics. You also might be genuinely curious. But when you ask this question, you break the romantic spell. You call uncomfortable attention to the obvious: “I know I’m not the only one you’ve met on there.” And it just doesn’t need to be said.

There just is no right answer:

“Oh it’s going great. I’ve had so many dates. Who knew that getting laid could be this easy?”

“It’s terrible. No one will write me back.”

“It’s hard because most guys are such assholes.”

You either sound like you don’t really need to be on this date, or that you need it too much, or you come off sounding like a beleaguered, judgy prick. It’s a lose-lose. It also puts you in a tempting position to denigrate those who’ve come before this date, and it’s an uncomfortable foreshadow (“What will she say about me tomorrow?”) Save the dishing and piling on and other fun nastiness for your friends.

Case in point: A guy I met on OKCupid a few years ago asked me what I thought of the site. When I gave a vague response, he jumped in to tell me how horrible it was: “The women in New York City are such gold diggers, always making you pay for shit.”

SHSD image

Need a little extra help in the dating dept? Check out my online workshop–risk free.

We were at a tea shop at the time, and when the check came I whipped out my wallet so fast—I felt pressured to prove that I Wasn’t Like Other Girls, and certainly not attempting to work him over for an earl grey. But he was all, “Nah, don’t worry about it. I got this.” The whole thing left a bad taste in my mouth. He only had bad things to say about the women he’d met. And yet the only thing they had in common, as far as I knew, was him. He texted the next day; I never wrote back.

Asking how your date is faring romantically is the fastest way to suck the sexy tension out of the room. If you wonder why your dates feel more like interviews, it’s because you’re treating them like a job fair (“Got any good prospects?”).

I’m all for honesty, but not to the extent that you let fly your wrath or judgment or even mild disappointment—directed at an entire gender, population, or unfortunate dates. (See also: Talking about your ex on a date. Another no-no). You risk painting yourself the bitch, the dick, or the victim. And none of that looks good on you.

Plus, in all honesty? It’s really none of your business. I say that in the best way possible. It literally isn’t—so why burden yourself with more info than you need at the moment? Just because you’re sharing tapas with someone doesn’t give you access to their entire personal backstory, nor do they have access to yours. It’s a date; it’s a time to be choosy, and to ask questions you really want the answers to.



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Don’t hate on Valentine’s Day.

It’s easy to pile on poor Valentine’s Day. And if it makes you feel any better, a rather small slice of the population is really psyched about it.

If you’re single, chances are you roll your eyes, flip couples the bird.

If you’re in a long-term relationship, maybe very long, this holiday makes you nostalgic for the days when romance was new, before either of you peed with the door open, and when you had time or interest in having sex more than once a month.

Then again, if you’ve just started dating someone, Valentine’s Day is too much pressure. What if he thinks it means more than it does? What if it doesn’t mean enough?

And if you’re one half of an unhappy couple, this Hallmark holiday hits a nerve: Another year of not being in the relationship you always thought you’d be in. You may suffer a bout of brief, intense existentialist grief.

Basically, the only ones doing what you think the holiday is about (roses, chocolate, sex) are, if we want to get technical, people in the first 12 to 18 months of their relationship, who are still trying to impress each other, and guaranteed to get laid. Or, those blessed to be in one of those wonderful relationships where the magic burns for years. They’re rare, but they do exist.

Anyway, look, that’s not a LOT of people having sexy time today.

Valentine’s Day is not an exclusive club; it’s a holiday to celebrate love in all its forms, from the short, sexy bursts to the long, mellow partnerships, to the kinds of love we share with people we’re not dating. (Check out this study on how just being kind and loving to people at work is linked with improved productivity.)

But of course my heart is with the single people who see red at Valentine’s Day, and not in a good way. Here are the things I recommend you do and NOT do today:

1. Don’t hate. It’s not only pointless to hate on a holiday; it’s disingenous; like saying you hate money just because you don’t happen to have any. Don’t pretend that of all days, today you “hate” love because Valentine’s Day ruined it for you. C’mon. (That’s like “hating” gifts because you’ve had a few bad Christmases.)

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>>DO: Take a risk. You want something exciting? Try doing something exciting. One Feb 14th, I wrote a note on a cocktail napkin on slid it across a cafe table to a handsome thing. I never heard from him. Don’t matter. It was thrilling and empowering and kind (because though he never called, don’t tell me I didn’t make his day). I felt…romantic, without anything else having to happen. (Also: Read why you should be getting rejected more.)

2. Don’t go out with your girlfriends and dance in a circle. Sure, it’s fun. But the dopiest thing ever is when a bunch of single ladies who would like to meet potential mates do the one thing that will ensure they don’t: Turn in the lady wagons. Who-hoo! Girl power! No. This is dumb. Don’t form a big resentful clot in the middle of the room, telling dudes to talk to the hand. Why act like men suck, when, if we’re being honest, you’d like a nice one?

>>DO: Go out to meet people. If you’re smart, you’ll go out with just a few friends or, if you travel in a gaggle, split off and mingle. Or, forget the girlfriend outing altogether, and do something really bold: Go sit at the bar by yourself just long enough to enjoy a glass of wine. Remind yourself that you’re open to what may or may not happen.

(Afraid of getting rejected? Here’s why you should seek it out more.)

3. Don’t text your recent ex. I shouldn’t have to explain this. But, no matter how it ended, if you broke up within the past six months, steer clear. Of course, unless he has come back with a dozen roses and wants you back, and you’re happy about it. But if you both ended it for all the right reasons, going back now for a moment of comfort could cost you more later. (Read why you should unfriend your ex.)

>>DO: Go on a date with a stranger. Yup. I promise you, there’s someone online who’s free tonight. And don’t give me this crap about how it seems desperate. You can drop a line in the water and see if you get a bite. You don’t have to meet The One. But you can go out on one date with one new person, and say that on Valentine’s Day, you made an effort, and you had a reason to put lipstick on.

The moment when you’re headed out the door and the night is nothing but potential—that’s fun. And romantic. And brave.  And way better than a margarita-sodden rendition of “I Will Survive.” Again.



SamanthaDating an older woman is hot. Ask any man who dates one. And as a woman over 35, I’ve never felt more desired by men in their late 20s and early 30s than I do now-moreso even when I was that age. So if you’re only seeking women in the 21-29 age range, let me tell you, you’re missing out. Big time.

So why are men dating these ladies? There’s the ol’ elbow-jabbing, wink-wink idea that cougars* are more likely to put out and pay for everything. Meh, that may be a reason a naïve man attempts to score with an older woman, but not the reason he dates one.


She’s got her own life. And by that I mean: her own career, her own friends, her own apartment, her own money. A 30-year-old man from Brooklyn told me this is what makes independent women a turn on. “I find it comforting to know that her life goes on when I’m not around,” he said. Great if you have a life of YOUR own, i.e., dread clingy girls who abandon their own ships the moment you have sex and set up camp on your shore. Also, the fact that an older woman has her own money means she likely worked very hard to get it. Should you automatically go dutch or expect her to pay? No. In fact, you want to impress someone, take a lady out with some bank because she knows exactly how much that costs.

She can hold her own. This ain’t her first rodeo. So when you take her out with your friends or coworkers, to a wedding or work event, you don’t have to worry she’ll perish without your constant attention. She’s been to enough of these things on her own to manage just fine while you’re talking to someone else. And unlike the 23-year-old who gets tanked and throws shade at your ex, she’s got class. In fact, your ex will likely friend her on FB (like my old bf’s ex-wife did).

She knows what she wants-and doesn’t want. And at this point, she’s not afraid to say it. In the bedroom? Go ahead and try to shock her. Bondage? Bisexual encounters? Threeways? Role play? If she hasn’t tried it herself, she’s likely considered it. If you’re curious about the intimate lives of the older woman, I’m sure the videos over on can provide a good insight into what you’re missing out on. But I’m talking outside of it as well. You may buy into the idea that all older women are “desperate,” and some are, but many are not.** She’s choosier, and, unlike the 26-year-olds who think they’ll drop dead if they’re not engaged by 27, married at 28, and prego before 30, she’s looking at life a little differently now. Doesn’t mean she doesn’t want marriage/kids, because she might-but she’ll be pretty clear about it if that’s the case. Since she’s got a little life on her (and maybe even a marriage in her past), she may not have the rigid checklist that a younger girl has. Most of the single women I know over 35 just want a good man, period.

She doesn’t move in a herd. I aw a young man from Queens for a spell who dated older women exclusively because younger woman, he found, couldn’t do a thing without checking in with 15 of her friends. When you date a younger woman, he said, you also date all her friends, and it’s “a pain in the fucking ass.” You can’t just go out and do your own thing because she must check in with a larger governing body. A slightly more mature lady has friends-but she sure as shit doesn’t need to update them with her every move.

She had sex before she had a FB profile. Hard as it may be to imagine a world before Facebook, fact is, there was one-and I, along with many of my lady cohorts, lived in it. Given that we didn’t suckle at that digital teat so early on like female Millennials, we’re not going to live and die by whether we change our relationship status. I even forget it’s there. Get this: I’m not even FB friends with a guy I’m currently seeing. I’ve found it refreshing. It retains a bit of mystery, privacy, for now. I don’t need to be omni-present, liking everything he says or does, and I don’t have to monitor what I say, worrying it’ll be taken a certain way. I did get a glimpse of his page when he left it open one day, and I did take a gander at his ex, but I found it so stressful I closed out of it, thankful every comment from her wasn’t on my daily radar. Try getting away with that with a 27-year-old.

She doesn’t need you; she wants you. If she’s gotten this far on her own, regardless of whatever relationships are behind her, she’s been through the ups and downs to know she can handle just about anything. And she knows she won’t fall into a million pieces if she doesn’t have a boyfriend. But she would love one, for sure. And whereas younger women are putting you through the paces to see if you can provide her with a life, an identity, and a future, an older woman already knows who she is and what she wants to do-she’d just love someone to share it with.

She can make you a better man. A friend of mine dated a 40-year-old woman when he was 22 and new to New York. “She picked the restaurants, paid for things, took me places. She had access to a world I didn’t, and she had done all the things I hadn’t done yet,” he said. Now he’s in his mid 40s, married, with a kid, and remembers that relationship as critical to making him the man he is now. “As a dude, I’m told that I’m supposed to date girls my own age and take care of them, pay for dinner, and so on. But for that period of time, the roles were reversed. She had the power. And it felt great-who doesn’t want to be taken care of? That’s when I understood what it was to be in that role, to be someone’s bitch, essentially. And I could appreciate it when it was my turn to take care of someone else.”


*A note on cougars: The general consensus on cougardom is not so much a specific age as it is who you date. So, if you’re 35 and dating a 37 year old, yeah, not a cougar. But if you’re 35 and dating a 22 year old, ok, you might qualify. As might someone who’s 55 and dating a 30 year old.)

**There is a caveat here: Older doesn’t always mean wiser. And someone who was impossibly needy at 25 may be even moreso at 35, especially if she hasn’t had the relationships she’s wanted. There is, however, some considerable perspective and confidence that comes with age, and the more evolved women will exude it.


Originally published here on The Date Report.