So you think it’s time to have The Talk. You like each other, and you want to know the deal. You want to know where things stand.

Don’t do it. In fact, delay that conversation as long as you possibly can, especially when you’ve just started dating. My rule of thumb is that you can and should get to know each other for 3 to 6 months before you’re going to start slapping down rules and regs. Because the first person to bring it up loses.


Try not to have the talk for the first 3-6 months.

The need to have The Relationship Talk may seem all mature and adult, but really, it’s just you scratching an insecure itch. You “need to know.” I counter with this: If you’re having a fun, great, sexy time, why oh why would you drop those dreaded words, “Where is this going?” It’s the relationship equivalent of walking into the middle of a great party, turning off the music, flipping on all the lights, and saying, “So, I just want to check. Is everyone having a good time?” At this point, you might think its a better idea to just enjoy some videos from websites like and your favourite toy instead of dealing with relationship stuff if you are only in it for fun.

I did this a few years back. And I regret it and would never do it now. I had been seeing the guy a few weeks. He was a bit of a tough read, and I got insecure. I thought I’d help things along or feel better by asking, “So what is the deal, I mean, are we seeing other people, or…” It was a moment of weakness. Big mistake. The whole tenuous, if promising, thing collapsed on itself a short while later. And while that wasn’t the only reason, I sped it to its short and brutish end. Like driving into a wall at 60 mph.

Feeling pain, confusion and heartbreak? My Break-Up 911 online workshop is going to gently get you back on your feet. You’ll find confidence and optimism when you need it most. Come on over!

I’ve also been on the other side, by the way, many times. I gently tried to back off this very conversation with partners because it felt like I was being asked to make a decision I wasn’t ready to make. I felt pressured to say what I think he wanted to hear, and if that’s your idea of honesty, well. It’s not. I’ve often found myself marking time FROM THIS TALK, wondering who would be the one to bail out first. Why create this pressure when you’re really trying to get to know someone? Keep it a little gray–a little mysterious. This is how you keep that intrigue alive.

Ask yourself this: Why do I need to ask? What do I really want to know? What do I hope to accomplish? And while I can’t purport to read your mind, I’ll assume you’re craving what most humans do: significance and security. You want to know what’s going on, not because you’re conducting an investigation, but because you want to assuage the nagging fear and be reassured that you are special. You already are–can’t you tell? Nothing is totally secure in love and life, and no one owes you a sense of security.

And if your reason is that you’re afraid he’ll meet someone else? He could meet someone else regardless. There’s always that risk. What would happen if you held off on the grand summit meeting and just enjoyed the person without worrying about how to categorize or title or otherwise claim him? You get the best of both of you–and your own privacy, too.

“But I want us to be honest with each other!”, you cry. You can and should be open and communicative, yes. And after a few months you really do want to get serious, and you want a committed relationship, then of course you owe it to yourself and him to discuss it. But then-not now.

When you do feel the urge to have a meta-conversation, tell him (or her) instead about how much fun you have with that person, how much they rock, how attracted you are to them–and welcome those comments from him. A few sincere words about how you feel about that person can go a long way to making you feel more secure and appreciated. Early on you want to nurture growth, connection-not start laying down the law.

And that why having The Talk too early is horrible because it starts with “I like you a lot” and ends with “and this is what I need you to do/not do, etc.” It legislates. It kills the fun. It says, “Ok, so shall we look at the fine print?” Unless you’re about to close on a house together or do something else that’s legally binding (like marriage), there’s nothing to be gained by this conversation when you’re just starting to create something real.

There will be plenty of time to make it quite clear what you want, and then, if he’s unwilling to provide that, you’ll know you have a decision to make.

Also: Don’t confuse honesty with security. You think that if you know more about what’s going on under the hood you’ll feel better, but that may not be the case. Do you really want to know he likes you a lot but is getting over a crush from last summer, or that his ex-girlfriend has been calling again? Does he want to know you’re sort of weaning off this other guy? No, no, and no. Not your biz, not his problem. It doesn’t matter. What matters is that you keep choosing to spend time with and enjoy each other. It’s the actions that matter, not the definition of those actions. You don’t have to kick the tires every two seconds. Just drive.

Oh–and fuck your Facebook status. Honestly. If you’re making relationship decisions so you can click a box, I fear for your future. Because checking a box has driven more than one person into relationships–and marriages–that shouldn’t have happened. Labeling your life isn’t the same as living it.

Case in point: A client of mine has kindled a connection with a man who lives states away, and a good chunk of the year overseas. She wants to know if he’s her boyfriend or if he could be, and worries that by not nailing it down she’s being played. I tell her, yes, it is a game-and the goal is to keep the ball in play. You do this by maintaining a rich and vital connection, staying in touch and letting that person know you’re very much interested. As soon as she tries to get him to submit to certain rules or titles, I warned her she’ll scare him away, and he’s already far away.

Let’s get one thing straight: That discomfort you feel? That excitement? It exists due to the simple fact that things are NOT SET YET. Enjoy it. Don’t suck the life out of it in an effort to make it shelf stable. If you’re still with this guy 10 years from now, there will be a point, sooner than you think, when you’ll wonder where the magic went. This nervousness and thrill is par for the course-and trust me, you’ll miss it when it’s gone.

Truth is, there’s no avoiding the pain of a break-up. In Break-Up 911, my online course, I’ll show you how to effectively experience it so you can get on with life as quickly as possible. Come find confidence and optimism when you need it most!

Courtesy of chanpipat /

Yes and no. And not the way you think. Can you be involved with someone who lives far away? Yes. Will it work if you attempt to adhere to hard-and-fast rules where you define the success of the relationship by how “true” to each other you can be, by how little you can be invested in your local lives and live only to Skype?

Yeah, that’s not going to work.

It’s all about the timeframe and the expectation. If you’ve been very serious with someone and he or she has to move away for a set period of time, that may be doable because there’s a deadline. Or, you’ve been long distance and there are real plans in place to move closer within the next year.

But if he lives far away and there’s no realistic time period when he will be within striking distance–like, ever–then you have to be realistic, too. This does not mean you have to cut this person out of your life; in fact, an annual or even quarterly reunion with a long-distance love can be amazing, and give you something to look forward to.

I am not, however, a fan of the eternal, long-distance pine. And I have had several long-distance relationships, and not a one of them lasted very long. But I don’t see the distance as what failed them; I see our severed connections as having suffered a lack of vision, not love or affection.

You can keep people in your life in degrees. Too many of us see our relationships as an on/off switch—they’re either “on” in your life or they’re completely powered off. I do not understand this. I mean, I get why people feel they need to do this, but am shocked at why we continue to think in this very stringent and joyless way.

I’ll share: I met up with a man I’d known years ago at a dear friend’s funeral, where we connected over our grief—and found we had more in common than just our loss. He was from New England, where I was at the time, but was living in Miami. For a while it was quite romantic—he flew me to Florida, he came up to visit, and it was really a lot of fun. It’s fun to want someone you can’t have all the time (so, ok, yes, pining does have its upside). There was some talk of him moving back up north with his job, but then something changed. He became all of a sudden unreachable, unresponsive. When we finally talked, he said he’d made the decision to stay in Miami, and that meant he didn’t know what the point of our relationship was.

Wow. OK. So at first I was hurt that he would make this decision essentially to write off the state and me without talking to me about it. But also, I told him the relationship didn’t need to go anywhere it hadn’t already gone—that I would be just as happy to see him when he was up here, or make plans to visit him there. I was willing to reimagine the relationship so that we were free to live our lives, and yet could still enjoy one another when we could.

He was not so open-minded, and so it ended. But the real loss there was that he felt he needed to 100% vaporize. And he took it all—his friendship, everything. I feel bad for people like this, who think that relationships are all or nothing, when they don’t have to be. It was my loss, but I also believe it was his.

My point is this: By all means, cultivate and enjoy connections where you find them. But don’t get caught up on the on/off switch. Life is long. You don’t know where and how people will find themselves back into your life or your neighborhood. Keep it open, flexible, and loving, and you really can write your own rules.

Got a question? Some trouble? A mini crisis? Send it my way. 

Courtesy of photostock /

I’m no stranger to asking out dudes. I’ve done it—slipped my number into someone’s hand, slid a napkin-scribbled note onto a table, approached a man eating alone at a sushi bar, even walked straight up to a very hot guy in some kind of grounds crew and invited him to call me. But I’ll be honest—while it can be sexy and fun, and a great experiment to honing and exploring your confidence, most of those dates never transpired.

Women like to be chosen, plain and simple. Even the big loud-mouthed ones like me. And if you do the asking, you aren’t letting the guy take that step. You undermine his ability and urge to initiate action. Another thing that could happen is that you set a precedent—that you will be the one to ask for everything you want, thus removing some initiative on his part.

Now, every time I say this, I hear from men who say they would love it if a woman asked them out. And some men may like this, sure. We ALL want to be chosen in some way. It’s how you make that choice known that matters. In my experience, when a man takes the role of asking, he is deciding, not just agreeing to what YOU want or (god forbid) giving in. Maybe you’ve asked someone out and it worked and you’re together and happy. Good for you! It works in some cases, sure. But in my own life, I was finding that when I was too aggressive or felt the need to “produce” the relationship this way, I was getting in my own way and actually hindering him.

Understand this does NOT mean a woman is just a passive piece of produce waiting to be picked up, palpated, and taken home. In fact, you as a woman have a very powerful role to play here because in order to have a man walk through the doorway, you kinda have to open it.

So, rather than wonder if you should come out of nowhere and ask him out like some kind of surprise romantic attack, or sit and wait like a stone, do the opposite—lay the groundwork for attraction. You can’t start a fire out of nothing. Think of your efforts at flirting, connecting, etc, as laying the kindling and creating the conditions for fire to spark.

How? BE interested, show interest, give him lots of opportunity to talk to you, be around you, and pick up on all your positive, attractive energies. Make it clear that if he WERE to ask you out, you’d say yes (without of course saying that).  No one likes being rejected, and so you want to be sure he gets the sense that he won’t be. Look, dudes don’t always pick up on subtleties. So don’t be too subtle. He can’t read your mind. If he mentions a sushi restaurant bar just opened near him, you say, “I live for sushi. I could eat it every damn day.” (Only say this if it’s true, which, in my case, it is.) Or maybe you just tell him what you think: That he’s almost too damn appealing to pass up. That’ll send a message.

When you allow and encourage that attraction to take root and get his attention, you don’t have to worry about whether you should ask him out. Because you won’t have to.

And if he doesn’t? Maybe he’s not into it. Or not ballsy enough. Two good reasons to move on.

Screen Shot 2015-02-04 at 5.31.33 PMCould you talk a little about what to wear on a date? How important is it to be comfortable? Also, if I’m dressing up to appeal to someone else, am I kind of not being myself? I tend to look somewhat casual, but if I dress up too much than perhaps sending a false picture of myself.

–Jenna P., Boston, MA

Some people will say: Ah just be yourself. Be comfortable. The right person will love you for who you are, not what you look like.

Do not listen to these people.

How you present yourself has everything to do with how people perceive–and treat–you. Sure, I like to be home in a tank top and no bra. That’s comfy. You better believe I’m not leaving the house like that. And it’s pretty safe to say that unless they’re on their way to a big board meeting or a black-tie affair, most people tend to be fairly casual. This is besides the point.

The only time you really want to factor in comfort is when you plan to walk 5 miles or are investing in Goretex boots for a climb up Mt. Washington. And unless you routinely buy shoes that don’t fit or clothes that are uncomfortable, this is a non-issue.

Comfort Is Overrated

The comfort you’re referring to has more to do with confidence than it does elastic waistlines. Dates–especially first ones–are definitively UNcomfortable. By design. Showing up in sneakers and jeans is not going to remedy that issue. If you can bear the discomfort of a date with a stranger, you can bear up in heels for a few hours.

Why? Because how you look matters. Attraction is first and foremost visual. It just is. A man may not know Louboutins from Lululemon, but he knows a woman who’s made an effort when he sees one. And he can easily spot someone who hasn’t. Yes, a great sense of humor, intelligence, a loving nature, good soul–all important. But no one knows that when you walk in the door. They just see you–and if it’s you in a pair of ill-fitting jeans and a top that screams “I just threw this thing on,” well, you have limited yourself and the potential of this date.

Going out, meeting new people, and sussing out attractive potential partners isn’t about comfort. It’s quite the opposite: It’s about getting OUTSIDE your comfort zone. That’s where the magic happens. You want the ultimate in comfort? Stay home.

I’ll even go so far as to say that you should wear something that’s just uncomfortable enough that it makes you aware of your body, your posture. A pencil skirt with a slit up the back will make you aware of how you’re holding yourself on a bar stool, for instance. A fitted dress ensures you stand tall. Slight discomfort heightens awareness of your body, your physicality, and this can be a very good thing.

Now, that said: Nothing screams insecurity like someone who’s in clothes they don’t believe they can pull off. Hobbling down the street in sky-high heels is not a sexy look, even if some women from the likes of and other adult sites can pull it off and look sexy, doesn’t mean everyone can. Aim for confidence over comfort. Meaning: Yes, you should be able to walk without support, but you also want to wear clothes that flatter you and that help you look and feel more confident. It goes without saying that you shouldn’t invest in clothes that do not fit or cause you serious pain.

If you don’t feel sexy in fitted clothes because you’re sensitive about your belly, then you wear a top that flatters your midsection while playing up your rack, if that’s one of your assets. Great lipstick if you’ve got full, sensual lips. I mean, this is basic fashion advice right? Play up what works, play down what doesn’t. It doesn’t matter if you wear kitten heels or stilettos–it’s whatever puts a little swing in your hips and makes you feel like sex in a bottle.

Take this quick test when you look at an outfit:

–Could I just as easily hang out on my bed reading magazines in this? (Change out of it immediately.)

–Would I wear this very same thing to a baby shower or a work meeting? (If yes, it’s probably a little dull.)

–If this outfit could speak, what would it say? “I’m on my way to a 6-month cleaning” or would it simply purrr or perhaps even growl. Go with that one.

–Did I wear these shoes to clean the garage? Would they be aptly described as “practical?” Change them. Shoes are the punctuation to your outfit. They should say something, and it shouldn’t be, “I wore these for five hours in line for the iPhone 5.”

Is This Really Me?

It’s clear what you’re really getting at here, and it’s not so much what looks good on you (because I think you already know, and if not, go shopping with an honest and stylish friend). You’re really asking, “If I make an effort, am I not being true to who I am?”

What you’re assuming is that there’s only one “true” you. That the “real” you is in your underwear watching Honey Boo Boo Child, or in work pants and a sensible button down eating a pita pocket. Well, tonight the “real” you is going to wear a silky top and a skirt and slurp down oysters.

You aren’t choosing whether to be you or not to be you when you get dressed to impress. The idea is, how do I broadcast my best self. You don’t become someone else by sliding on some heels. You simply unmask another side of you.

I’ll go so far as to say this, too: Not making much of an effort is passive aggressive. It says, “I shouldn’t HAVE to make an effort.” Or worse: “Prove to me why I should.” Eeesh. This sends a message not just about how you feel about your appearance, but about how you view relationships. If you don’t make an effort now, why would you make an effort at any other point? It may start with lipstick and raking a comb through your hair. But it becomes how much of an effort you make to listen to and understand him, how invested you are in keeping your passion alive. Being accountable and willing to rise to the occasion matters.

Girl Shows Up to Date Unshowered

Case in point: A male coaching client of mine went on a first date recently–a brunch date. Turns out the girl figured since it wasn’t a Saturday night, she had license to be sloppy. Unless you’re a French model, the just-woke-up look won’t work for you or most. He reported that she made no effort–no make up, hair a mess. He got the impression she fell out of bed with a hangover. It was a turnoff.

“Is it crazy to want a girl who looks put together with some effort? Just not sexy to me if you didn’t try,” he wrote to me.

No, it’s not crazy. Not at all. You don’t have to get all tarted up in a way that’s unnatural to you so that you can get the guy to like you. But you do have to turn up the dial. And if your instinct is to reach for what’s merely “comfortable,” rethink it. When you make an effort to really shine in your appearance, you send a message not only that he is worth that effort, but that you are, too.

Got a dating or relationship question? Send it along to me via

Terri Trespicio is a writer, speaker, expert, and coach.