How hard could this be to turn down?

An old friend of mine moved back to New York and before he found an apartment, the guy has dates out the wazoo. Here’s a man who knows how to make it happen. You know how? He asks. He asks a lot of people. He shows interest in lots of ladies online and doesn’t hang in the email limbo, but gets to it and sets up dates and goes on them.

He doesn’t limit himself to the faux rules people draw up for their dream dates (and neither should you). Which means when he came across a woman he found particularly fetching, he didn’t care that she set a lower height limit of 5’9 (my friend is 5’8). He did acknowledge it, however. “I realize you’re looking for men 5’9 and above, but I would really like to meet you.”

She responded that she was willing to bend that requirement if he was ok with the fact that she “really really hates football.”

I told him I wasn’t as concerned with her not liking football as I was about her having such strict rules to begin with. I wish I could hop onto his account and write this girl back myself and say WTF ARE YOU DOING?! Because she’s worried about matching likes/dislikes before she’s even met the dude. Who cares if he likes football? (See: Plenty of happily coupled folks who part ways during Monday night football).

This is where online dating went wrong. The ability to choose preferences has misled you into thinking you can find exactly what you plug into the machine, as if this is a remake of Weird Science and not a filter for meeting actual people. In fact, your list of preferences may very well be the thing that’s keeping you from finding anyone. Because you think you’re writing up a list of prerequisites for a job you’re filling, when really that position is created anew with everyone you meet.

The likes and dislikes are what you learn as you get to know someone, not boxes you check before you do. Because you won’t actually get to know anyone that way if you cut potential off at the knees–especially when it’s a thing that, let’s face it, lots of dudes like. If she rules out ANY guy who likes football, she may be ruling out a lot of wonderful potentials, just because she can’t sit through one sport. #fail.

Newsflash: To love and be loved someone, you don’t have to be perfectly paired on every single thing. You’re not looking for a twin; you’re looking for a partner. And while of course you’ve got to have some things in common, those don’t have to be hobbies, but values, humor, aesthetic–they all play a part. But what I wish for you more is that you find someone who does you one better than match exactly what you like–who expands your world, and your comfort zone, and gives you the courage to try new things.

The profile is not the key to real connection. You won’t ever know what you think of someone until you meet them in person, period.

Think back to the old fashioned way of meeting someone: You get introduced, or maybe you see each other at a party, make eye contact, start chatting. Maybe he gets a job in your office and you see greet each other getting coffee every day. Maybe you wouldn’t have picked this guy out of a lineup of potentials, but he makes you laugh–a lot–or becomes more interesting the more you talk.

Sometimes you’re hit over the head by someone you see and think “Him!” but there have been so many times I’ve been pleasantly surprised by how incrementally more wonderful a person became. A girlfriend of mine confided about her fiance, “He was an average-looking guy on our first date, but he just got hotter every time I saw him.”

So you see how this works, right? And how some prefix menu of attributes, likes, and physical characteristics is something you made up, and doesn’t necessarily predict the person you could really love. You go in with your heart set on finding a man 6’0 or above, who is Buddhist, gluten-free, and passionate about soccer and Siamese cats, and you miss out on the hilarious meat-eating Jew who hates soccer but is crazy good at table hockey, owns a labradoodle you fall for, and makes you feel like the sexiest woman on the planet.

Stop treating yourself as a bouncer to the door of your dating life, looking to turn away anyone who approaches in the wrong shoes. Try not to strictly limit your playing field in the name of what you think you like, and allow yourself to be surprised once in a while. I don’t know if my friend ever went out with that girl, but in my heart of hearts I hope that she does, and as she laughs hard at one of my friend’s silly jokes, says to herself, Thank God I didn’t let a sport I don’t like dictate who I meet. 

Because you shouldn’t, either.

Reading_glassesI don’t look or feel that much different than I did two, five, even ten years ago. In fact, I look better now, thanks to having grown out some questionable haircuts and dropped gluten from my diet. Certainly, no worse for the wear. I still get carded (wherein I blush and make a fuss).

But there’s one area that is aging right on cue: My eyes. They, seem to be losing their ability to focus. Like the rest of me.

I’ve been wearing glasses since I was in the second grade, when Orphan Annie had her own line of plastic lens wear and I sported my pair proudly. My face has been framed a hundred different ways thanks to shifting tides in eyewear trends over the years. So getting glasses was not the hurdle here. It was ordering “progressive” lenses that pushed me over the edge.

The way I understand it is this: The flexible lens inside your eye that enables your focus functioning becomes increasingly rigid over time, making it harder for you to see clearly what’s right in front of you. I caught myself holding a menu further from my face and squinting at the computer screen–trademark middle-age moves, and was like, Holy shit.

“You must be close to 40?” my eye doctor asked.

Um, yes, as a matter of fact.

“Yeah,” she nodded, looking back down at her notes. “That happens. Completely normal.” This was very underwhelming.

And ironic. You spend your whole life trying to be normal, like everyone else, better than normal. And then, you’re told that you are, at last, exhibiting the standard markers for normal human aging, as your body breaks down according to plan. It’s very disappointing.

“Unless you wanted to carry around half a dozen pairs of glasses everywhere, the progressive lenses make sense,” she said. “Eighty percent of my patients over 40 use them.” Double oy.

The term “progressives” is a fancy update to “bifocals.” They’re actually quite a technological breakthrough–they’re multifocal, allowing you to shift prescriptions depending on where you look through the lens. I don’t know what mathematical genius came up with a way for a lens to do this, but I am prone to violent motion sickness and anticipate the adjustment being a very bumpy ride. Still, somehow they were able to fix this by measuring the pupillary distance for my new glasses, making the adjustment period a little easier for me. (They haven’t come in yet, so I will report back .) The pupillary distance measures the distance between the center of your pupils. Opticians use this measurement to ensure that the lenses are eyeglasses are correctly aligned.

The problem is the only people I know who wear them…are my parents. Sigh.

So I did it. Ponied up the cash for progressives, the way I imagine people make these kinds of concessions, because it makes sense, the way you might hesitantly say yes to horrible orthopedic shoes. A walker. Adult diapers.

But for now, it’s just glasses, which I’ve worn forever anyway. I’m trying not to make it a thing. (Too late).

This is, in effect, the body’s poetry: It teaches you a kind of wisdom through its limitations, in the way it changes your perception of the world around you. I haven’t been able to see further than four feet in front of me for as long as I can remember, but I’ve always been drawn to the big picture, to what’s out there, what could be and might be, at the sacrifice of focusing on the details. I find it excruciating to concentrate on one thing, one project, one draft without my eyes drifting away to something bigger, easier, further to reach for.

One of my roles is VP of Business & Talent Development at 2 Market Media, where I identify and cultivate talent–which I do by coaching experts to be powerful media personalities, and by developing content, looking down the arc of their story and brand. That feels so natural to me, to think and focus on their big picture, which is a safe distance from me. But when it comes to my own brand, my own projects, well, that’s a bit too close. Things get blurry and hard to see.

It plays out in other ways too–it’s also why I ask for a fork when there’s one right next to my plate, or why I went out and bought a magazine that I already had on a shelf. I keep missing what’s right in front of me, and it can be annoying, or worse.

This is a challenge for all of us. So much of the self-help lingo is about the big picture, knowing where you’re going, and I get that and how important it is. But especially as you get older, I realize that I can’t lose sight of what’s right there in front of me. And neither can you. Until we can see what’s right in front of us, we won’t get where we need to go.


The hammock I should be enjoying on the beach I should be visiting.

Everyone mourns the end of summer. I always did, too. I’d get nostalgic and weepy as a kid, watch horrible VHS tapes of a family trip to the beach, make mix tapes of songs that I could sob over in September. Ah, summer, so delicious, fleeting, and sweet. But was it? No, it never was. Summer would leave you high and dry and be gone before you knew it.

Honestly? Summer can suck it.

Sure, it was a big deal when I was in school, and summer meant things actually changed. I was temporarily freed from the chains of academia, and free to bake myself in my own driveway wearing SPF 4, wait tables till 11p and then hit the diner with the staff. Go to the beach. Make out with another waiter. It was fun sometimes. Other times, I thought of other stuff I should be doing.

And that’s because the images and fantasies we have about summer are a lot of pressure to live up to–even without social media to contend with. One summer when I was 26 and living with my sister in Newton, MA, I begged her to walk with me down Centre St. to get ice cream one evening in July. We had to.

“Why?” she said, looking at me like I’d lost my mind.

“Because this is what you’re supposed to do during the summer! You’re supposed to walk lazily down the street with an ice cream cone. Come on!’ We did go, and I ate it, and then felt sick. Because I’m lactose intolerant, but I wasn’t going to let that stand in my way.

Summer is a microcosm of life, of youth–and there’s so much you feel you should be doing in such a short amount of time that it’s hard to do what you want. I should be sitting on a beach, I’d think. I should be reading a bestselling novel! Why aren’t I reading more novels! I should be using more sunscreen–but I should also be more tan. How do you do that? I should be dating someone! Or if I was dating someone, I shouldn’t be dating someone! I should be single! Aah! Aaaaah!

Part of me is relieved that life doesn’t undergo such a transition anymore just because it’s summer. Other than a temperature change and a wardrobe shift, not too much else is different this side of adulthood. Yet even here, in the city I always wanted to live in, I groan at the thought of all the summer concerts I never attended, all the margaritas I didn’t drink on rooftop bars downtown. Shit–should I have been doing that? I recall the day back in June I bought a sweet new two-piece, with visions of where I’d wear it. Poor thing only saw a single dip in the pool at Treasure Island in the dead desert August heat after a trade show. Boo.

As if my own made-up fantasies weren’t torture enough–hello Facebook, where we bear witness to what is essentially an endless scroll of summer postcards, depicting blissful, seasonal utopias. I know it’s curated, but it’s still lovely: back-porch BBQs, yawning blue skies, the bright bellies of surfboards slicing through surf, tilting, sunny portraits of beaches and crab boils. Everyone making easy jokes in breezy cotton tunics and slide-on shoes.

Summer is such a FOMO hot zone that I welcome the steady Back-to-School drumbeat. I fucking love it. I’ve never been good at guilt-free lounging. OK, folks. That’s it! Time to fold up those chaises and pack it up. I’m sitting in the parking lot, revving the engine, hurrying your sandy asses up so we can head back to the real world and leave this season in the dust.

So I can get back to business. And start worrying about what I’m supposed to be doing for the holidays.

Screen Shot 2015-03-29 at 11.51.26 PM

So that’s what gluten free singles look like!

You may be single, and unable to eat wheat, but there’s hope for you yet. Why? Because now there’s! Why would you ever bother with another bread-eating boyfriend again when you can rule them out altogether? Quinoa lovers only, please.

I’m kidding of course. Because if you’re going to start limiting your selection of people to date based on what YOU can’t digest, you’re in trouble.

I’m a gluten- & dairy-free eater (with very rare and usually regrettable exception). This is my personal dietary issue and I deal with it. But why in the name of spelt would you add another qualification to your list of People You Can Love? You don’t need another dealbreaker. You need to open yourself up to more options, not fewer. If you believe, truly, that the right man (or woman) for you will be someone who must also shun baked goods, I gotta ask where your priorities are.

I’m willing to concede (but only slightly) with vegan. And not just because vegan is a serious commitment, but because it’s often driven by ethical issues–issues that could get in your way if watching a man moan blissfully into his burger makes you seethe with utter contempt. Ok fine. Stick with vegans then, or at least people who are somewhere in your neighborhood (lacto-ovo, perhaps).

But unless you have Celiac, and only a fraction of the population has it, chances are you’re gluten free for a host of other reasons, any of which might be linked to mood, diet, weight, etc. It may be a real restriction, or it may be a preference. But it’s probably not ethical. Not too many people are picketing pancakes because it’s unfair to the flour.

So no, you don’t need a partner who’s sensitive to wheat. You need a partner who’s sensitive to YOU and your needs. That’s it! I had a boyfriend who went off gluten just to try it, and stuck with it long enough to lose 15 pounds and feel awesome, but gradually went back to it because, well, he could. He appreciated the experience, and was aware of my choice, and that’s it. End of story.

Don’t go limiting your love options the way you do your menu options. You don’t need matching leaky guts to be in love. He can love you, even with all your cute little gluten-free flaws.

Read my tips for not letting your g-free life get in the way of dating. Such as, please don’t talk about your bowels at the table. Ever.


Doesn’t look like a weapon. But it can be used as one.

Living in New York City, you’re going to get a heaping dose of crazy on an almost daily basis. It’s just how it is. It’s inconvenient, annoying, but it usually doesn’t get violent–especially if you don’t engage. For the past three years, I’ve slipped by and around lots of it, unscathed.

Until a few months ago when my luck ran out–and I found myself on the business end of a cold beverage.

My (then) boyfriend and I were walking down W 70th toward Columbus, in fact TALKING ABOUT CRAZY PEOPLE because we had just passed a known nutjob who’d recently caused a ruckus in a falafel shop. And I was telling him about a man who hollered at me at a bus stop a month earlier. As we blissfully meandered down the street on a lovely summer day talking about crazies in past tense, one showed up, hot on our heels.

“Get out of my way,” came a strange voice from right behind us. We turned to see a man looking warily at us, clutching a black messenger bag with one hand and a coffee in the other. “Get out of my way,” he said again.

He was a black man, maybe late 30s /early 40s, with very dark skin, in a navy t-shirt and workout pants, and big, bugged-out eyes. We made way,  but he didn’t move.  After a tense pause, I decided it was best to keep walking.

Bad idea.

The moment I turned my back I was instantly doused head to toe in iced coffee. Cream and sugar.

WTF?! I wheeled around and the man started to retreat back down 70th the way he came. I was mad as a hornet (and got tougher the further he walked away). “What the fuck is your problem you fucking asshole you fucking–“ until Dru gently but firmly guided me eastward toward the post office where we were headed.

Now, if you’re ever assaulted in Manhattan or anywhere else, you can only pray that this is as bad as it gets. I was unharmed, if sticky. I had had nothing taken from me, and I wasn’t frightened. Just fuming. I called the police and filled out a report. I was lucky–it was 85 degrees out, and the coffee was cold.

(By the way, people get arrested for throwing coffee a lot. An extraordinary number of the instances I found occurred in the Boston area, and involved Dunkin Donuts. Having lived there for many years, I’m not surprised. Alec Baldwin cites throwing his 32 oz iced coffee at some hecklers in a cab the greatest moment of his life.)

What’s really the reason I was mad, though, aside from the obvious mess, the indignation at being attacked while minding my own business. This man wasn’t just insane, but threatening our way of life. Because you can’t do that. You can’t go around throwing things at people just because you feel like it.

The only real damage done here was to my ego. How dare HE do that to ME. As if his act of wacked-out behavior should somehow not have happened–because I’m what: Nice? Hard-working? Minding my own business?

And I was also envious. Because there are plenty of times when I want to throw things at people, but I refrain. This guy didn’t feel curtailed in any way by laws or social etiquette. He just did what he wanted.

But there’s also a lesson in there. While there’s nothing I could likely have done to avert the situation, except not leave my house, this shit just happens. It just does. Way worse things happen to innocent people all the time. It’s not fair that it happened to me, but also, anyone who was standing in front of this man would have been subject to his caffeinated rage. When things like this happen, you realize that there’s nothing actually special about you. Sometimes you’re just in someone’s way.

This single act was the manifestation of another fear you and I have, aside from being the victim of a violent crime: Rejection. Someone who doesn’t even know you judged you, hates you, and acts out on it (perhaps irrationally, but so be it). It seems unfair. Especially when I, like you, make a considered effort to ensure that people like and accept me–probably more than I should bother.

That iced coffee was in some ways a refreshing dose of reality. If I believe everything I do or say matters tremendously, that I control all that happens to me, including other people’s behavior, I might start to think I’m really important. That I’m fully in control. I might even have this idea that I’m powerful and good, and that Nothing Bad Should Ever Happen to Me. And that’s a high perch to fall from.

So for now, I’m duly humbled. My freshly laundered shirt is unmarred by the event. I’m reminded that I’m in a big city full of people with crosses to bear, scores to settle,  neurons that misfire, and who are generally batshit crazy.

Fear of what people will think or do is never a good enough reason not to do something. Because you never fucking know what will happen, and you can’t prevent or control it. You may get dumped. You may not get hired. Someone may hate you for no reason. And somebody will waste their hard-earned money to nail you with a cool beverage just because. And that’s what happens. Next.



Your love of a good story is getting in your way.

In his recent post on The Date Report, Ryan Dodge pokes fun at the tendency every couple feels to schtick-up their how-we-met story. He admits that his first date with his current girlfriend was forgettable at best. He asked her out again because she was hot, and why not. But he certainly didn’t stumble out of that date bleary-eyed with love. But he admits to feeling pressure to make it sound more interesting now, and so do you—even in the relationship you don’t have yet.

The pressure to have the best, funniest, quirkiest, most magical “story of origin” is not only given far too much weight, but it’s getting in the way of your meeting someone special—especially if you have an “idea” for how it “should” happen. When you jump ahead to some imaginary future dinner party and worry about how you’ll tell the story, you’ve made the mistake of believing that the opening scene is what matters most. You believe it so much that you will restrict how and where you meet people. And it’s a big fucking problem.

Look, we all love a good story. How DO people meet and fall in love? And for those of us who are doing the asking, we may be on a fact-finding mission to see if we ourselves have left any situational stones unturned. Who doesn’t love the tale of the soundtrack-ready romance in which an annoying fender bender on I-95 turned into true love? We love that shit! That’s why we go to movies!

But the expectation that every initial meeting must be a Meg-Ryan-esque moment where initial awkwardness melts into pure, unadulterated passion over a latte is silly, to say the least. Do not make the mistake of confusing your own real life here in the matrix with some dream Nora Ephron once had. (Writers, you are at particular risk here.)

When I sold a set of shelves to a tall drink of water last summer, I thought “ooh good story. This is how we can say we met,” except we didn’t last past two dates because he decided I wasn’t what he was looking for. I mourned the loss of the story more than him! So trust me, I get it.

Yet I’ve met more than a few single people (mainly women), who are so obsessed with the story of origin—of a relationship they don’t even have yet!–that they actually WON’T do certain things or go places to meet people because of how the story will read. Think I’m kidding? Nope. Or–OR–they will full-on lie about their story because they don’t like “how it sounds” that they met in a bar, or–gasp!–online.

Such as….online dating. Earlier in online dating’s brief, storied history, to meet someone online was dubious to say the least. And even now, with so many people hooking up online, still people feel weird about it. I don’t know why. I’ve met so many people online and in person that sometimes I forget exactly where I met them. I love that. The goal is to meet people, and to meet so many that you have to think really hard about whether you were introduced by someone or met online.

And yet, I’ve met plenty of people who literally refuse to post an online profile because what IF they meet an amazing person there and have to tell all their friends where they met? This is insane. Note, these are the same people who will whine that there’s “no one out there for them.” Really?

Online dating is not another planet where questionable human-like beings are beamed in from another galaxy. They’re the same people you would meet within a 10-mile radius of your home if you happened to be at the same watering hole. Instead, you were both online. I think this is wonderful. But you’ve determined it’s not a good enough story. Sorry. Do you want a story, or do you want a partner? 

How you meet doesn’t matter—that you met does. You go to lots of restaurants and bars and parties, and you’ve done your laundry a thousand times in the same room, and you will meet more people than you can remember. But when someone happens to catch your eye and you feel a stirring connection, ask yourself–does it really fucking matter where I found this person? No. 

It’s time you redefined your notion of story. In the interest of time and waning attention spans, no one at a dinner party is going to ask you to explain the entire arc of your relationship. They’ll never ask, they don’t care, and it’s none of their business, quite frankly. Stop thinking of your life in terms of its entertainment value to others, and more about what you really want—so you can stop limiting the ways in which you find it. 

Originally published on’s The Date Report.


If you’re not getting 3 strikes, you’re not trying hard enough.

If you’re weeping into a glass of sherry and wondering why the world is so cruel and your life is so loveless, well, you have no one to blame but yourself.

Yes, I said that. Because if you’re like a lot of women, you wait. And wait. You think you’re enlightened and independent, yet there you are clinging to this Disneyfied idea of romance, believing down deep that if you click your heels, the Right One will appear, if you just sit quietly and wait. It’s not the world getting in your way; it’s you.

You need to make shit happen. Here’s how: You need to take more risks. And you need to get rejected. In fact, my challenge to you is to get rejected no fewer than three times. Tonight, if possible. Because it means you’re getting somewhere. Also, because it’s unlikely you’ll even get that far before someone takes you up on it. (Trust me on this.)

Men already know this. They play the numbers. They’re used to rejection–they accept it as part of the game. If they ask out ten ladies, it means one or two or three will say yes. They go after what they want, and expect rejection. Regularly.

I knew a guy like this in college. He was nothing to look at, truly, but a fun, personable guy. He was never the hottest guy in the room. But he asked out EVERYONE. And the man always had a date. It’s not magic. It’s numbers.

You need to think this way. You don’t need to “act” like a man, but you need to adopt the mentality, create the calluses, and push through it. If you prefer a more gender-neutral example, think business: A salesperson doesn’t go into the field thinking everyone will say yes. But she goes out knowing that to get a return on those efforts, she needs to aim for far more than she’ll actually land.

When’s the last time you got rejected? And what did you do about it? If the answer is go home, lick your wounds, and stop shaving your legs, that’s the wrong answer.

I’ve gotten rejected lots of times–tons. It sucks every single time. It will always hurt. But it doesn’t always have to stop you cold. When I look at the past year alone, I’ve been told many times “no,” or “later,” and “maybe not.”

STRIKE ONE: I was seeing a man in the midst of a divorce; he had pursued me. Then he said he needed time; he’d be back. That was a year ago. When I asked whatever happened to him, he said he was dating other people, but decided he “didn’t want to continue our thing.” Our thing? Meaning, that thing he started? Yeah, that hurt. Moving on.

STRIKE TWO: I sold a guy a set of drawers on craigslist. I was charmed. I emailed him to let him know I thought so. We went for coffee. Then, a walk. He emailed me the next day and said I just wasn’t what he was looking for in a girlfriend. I was shocked, then hurt. Then, over it. Next? I couldn’t help but feel the need to find a dating coach; perhaps I was doing something wrong?

STRIKE THREE: I put the full-court press on a guy I met at a singles event (or rather, I happened to him–find out how to do this). I had him in the bag–I thought. He texted me the next day to go out. Then he changed the date. Then, he changed his mind.

I have more…you want me to go on? You get my point. I get hurt, sad. I don’t quit. And I’m never without a date if I want one. I just go get one.

I also find men wherever they are–not just out at some bar. Anyone you meet is game, and he doesn’t have to be in striking distance of a gin and tonic to be game. I recently visited the Apple Genius bar for help with my Mac. The guy who helped me was completely adorable. I started to leave after our session and then turned my ass right around and went back inside and, when I couldn’t find him, gave my card to another employee to give to him.

He wrote me back a very polite, service-oriented note. I wrote back telling him I was interested in him. And I didn’t hear back. For a month.

I forgot about it.

And then, weeks later, he started following me on Twitter. I called him out (“hey I know you”) and he replied, “We should hang out.”

So we did. And we are.

Be warned: The more time you spend in a gaggle of ladies, the less time you spend taking the risk of putting yourself out there in a real way–making yourself vulnerable, trying, and, failing. Failing isn’t a mistake or something you shouldn’t have done. It’s something you should be doing more.

Do it. Go out–alone. Look hot. Feel hot. Sit at the bar and get a drink. Start a conversation with someone who’s even just mildly attractive. I don’t give a shit if he’s married, gay, or about to enter the priesthood. Buy him a drink. You will probably not marry this man. But you may date him. Who knows? And at the very least, you have a fun, flirty conversation. There will be more.

Do it again. And again. Introduce yourself to guys you meet randomly, in passing, anywhere. Rack up numbers. And you will get results–and likely, a guy who appreciates a woman with a little initiative.


Terri Trespicio is a media personality & lifestyle expert, and a dating coach with expertise in getting singles back on the field. Visit her at and follow her @TerriT.


questioning_man1Ah, shit. I wasn’t going to blog about The Bachelor. And while I hardly hold it up as the shining and global example of all romantic relationships, it’s a pressure cooker wherein all cliches rise to the surface quickly, so let’s pluck a few out and look at them.

This week’s lesson: Bitchy and guarded do you no favors. If you’re at the center of drama, red flag. And if you hold back for fear of being vulnerable, you’re cooked.

This week, Sean let two women go: a bitchy drama queen who couldn’t play well with others, which is so obvious there’s nothing to say about it. And Lesley, the political consultant from DC who was afraid to be a fool for love.

(If you missed it and need a catchup, here it is.)

During what turns out to be her final date, Lesley admits to “us” that she’s falling in love with Sean. But she also says that she’s always considered the ladies of previous seasons, who confess their love, to be fools. Sean takes her to a fruit orchard, and this is her chance–to make it clear to him how she feels. She considers, and holds back. Fear of being a fool wins. 

He on the other hand, in all his tow-headed glory, says that while he likes her, he feels nothing is moving forward. He isn’t getting much of a read from her. And after all day harvesting avocados, the date is fruitless. He says she seems tense. Because she is. And guess who’s left without a rose? Exactly.

If we are going to draw any conclusions about this–whether it’s what this guy wants, the director wants, or what Men In General want, this is it: That holding back your feelings, playing tough and guarded, will cost you.

Does this mean that you should be gushing to guys that you are falling in love with them? Not so fast. But to connect with a person and maintain his interest, you have to do more than look smashing in a pink sarong. You need to give that person something to go on, a reason to return. You have to let someone know how you feel, and not make him guess. And yes it comes with a risk you must take–to risk being a fool. Sorry. That’s the game.


Courtesy of BrianHolm /

Sure, you could spend the night watching Love, Actually and then sob into some leftover Shiraz. Or, you could actually do something fun and maybe even sexy. No, it does not qualify as even the lowest level crisis that you’re not perfectly matched with an ideal mate just because it’s Saturday. If you are really lonely, use gay dating sites, or any other sites that float your boat, to spend the day with someone. You’re both in similar situations being single on Valentine’s day!

You’re single now, but you likely won’t always be. And mark my words, there will be a time when you look back and wish you had enjoyed this time more. Sure you want romance–and there’s nothing more romantic than potential. So, here are some things to do instead of taking a bath and then journaling about what a stark, lonely figure you’re cutting against the landscape.

Take a romantic risk. Consider it a wild card day. Do something out of character. Slip someone your phone number. Flirt. Post an online dating profile. Online dating wasn’t so popular a few years back but now, there are millions of people with profiles! You can sign up for any site that takes your fancy. You may want to use a BBW Dating site if that’s your type. The online dating categories are endless so there’s nothing stopping you. Or just ask someone out. I gave my number to a guy on a napkin in a cafe one year. I didn’t hear from him, but it didn’t matter; I felt amazing. Because of me, there was a little more romance in the air that day. I put it there. And so can you. And yes, this includes posting an online dating profile. (My tips on pics you should and shouldn’t use.)

Tap your sexy side. A bitch session over a bowl of nachos is not gonna fly.

Watch my Fox 5 NY segment on the topic

Gather your girls and sign up for something a little racy, like a class or workshop at The New York School of Burlesque (or your city’s equivalent), or a pole-dancing class (which is such the rage I can’t imagine you can’t find one near you). You might find a studio, like I have (S Factor in Chelsea, which has locations in other cities), but there are also private, pole-toting instructors who will come to your home.

Shop for free. This tip comes from my friend Melissa Massello, founder of Shoestring Magazine (great resource for fun on a budget). Tell your friends to gather up all the stuff that’s un- or slightly-used stuff they don’t need or want anymore, and you’ve got your own pop-up store. Think: nailpolishes, fragrances, mineral makeup, and other safe-to-swap items, like clothes and shoes, scarves. Great way to shake up your closet and clear out stuff you don’t want. Donate the unclaimed to a local charity or a non-profit like Dress for Success. Check out Massello’s helpful swap guide to plan your party.

Go from wistful to grateful. It’s easy to bitch about men. Too easy. Try shifting your perspective by taking stock of your great loves and good friends. Reach out to someone–an old flame, a former love, a good friend–and let him know how much he means to you, or meant to you in the time you shared. This makes you focus on how much love you’ve had in your life–as opposed to what you’re lacking. I did this one year and it felt great. Note, I recommend AGAINST posting public queries on your ex’s Facebook wall. Bad, bad idea.

Ok. Have fun.