The Pick Up: Valentine's Day Survival Guide

By Nick Savoy

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<p>Navigate all the hurdles Cupid throws your way like a champ. Playboy.com tells you how to survive Valentine's.</p>


Are you excited for Valentine’s Day? Really?

If you’re a man, that probably means you’re in a committed long-term relationship that’s going very well. If so, congratulations. For the rest of us guys, Valentine’s Day can be a minefield.

It can be tough to know what to do for Valentine’s if the relationship is undefined. You kind of have to guess. If she feels that you two are well on your way to being a committed couple, you’ll have problems if you ignore Valentine’s Day. But if she feels things are still pretty casual and you act as though the two of you are a committed couple, she might become less attracted to you.

It’s a weird aspect of psychology, but in general if the other person seems to care more than you do, you will become less attracted to them. There are many exceptions to this, and the solution isn’t to act like you don’t care at all, but it’s a good general rule not to over-invest.

The best plan here is to get information first. Ask her what she’s doing “next weekend” or, more specifically, next Friday. If she mentions that Friday is Valentine’s Day, say something like, “Oh yeah—that’s right! Hey, I heard that they’re doing a big chocolate buffet at [wherever] for Valentine’s, we should check it out.” That at least preserves a bit of ambiguity. If she says she has plans or doesn’t seem to expect to hang out, that’s a signal to lie low on Valentine’s instead. And then pick up afterwards as if nothing happened.

Valentine’s is probably not your favorite holiday. You have all the same issues that you’d have if you were casually dating one woman, multiplied by however many people you’re seeing. Plus, there’s only one of you, and only one Valentine’s Day, so it’s not like you could see everyone you’re dating anyway.

This has nothing to do with lying or cheating or sneaking around. You can date multiple women without lying. But where to spend time on holidays and special days can potentially be an issue.

If Valentine’s is going to be sticky, then leave town. For real. This becomes a great weekend to go visit whatever lonely relative you’ve been neglecting. Send flowers to each woman and call them on the day.

Go out. You’ll find that a lot of the women you meet are single. (On Valentine’s Day, stay away from women with guys with them. Just for Valentine’s, though—normally I strongly recommend approaching mixed groups.)

Be prepared for different dynamics. If a group of women are going out on Valentine’s Day, they’ve probably been thinking about and talking about their dating life, what they want in a guy, why men suck and so on. While most of these women will be genuinely looking for a great guy, a lot of them are going to have their defenses up. There’s a greater-than-usual risk of jealous friends sabotaging you as well. Be prepared for questions like, “Why don’t you have a girlfriend?” and “Why don’t you have a date tonight?” 

And no, it does no good to respond with “Uh, you’re out too, right?” Remember the Love Systems principle of Change her mood, not her mind. If she asks you why you don’t have a girlfriend, defuse her question with humor. For example, you can tell her that you have eight girlfriends. (If you want a sample dialogue for how to do this, click here.)

Congratulations. Valentine’s Day is like your bye week. You don’t have to worry about a lot of things that other guys do. I’m not going to tell you how to take your partner out on a romantic date—presumably you know her better than I do and you’ve made it this far. Instead, I’m going to give you some ideas for “extra credit,” stuff that some men don’t think about but that goes a long way with women when you’re already in a relationship:

Send her flowers where her girlfriends can see (e.g., to her work if it’s appropriate) Find out somewhere she’s dying to go and then pretend to forget all about it. Secretly make reservations for Valentine’s Day. Don’t tell her where you’re going, only what kind of shoes to wear. And then watch her smile when you pull up to the place and she figures it all out If you don’t normally dress up, do it when you take her out on Valentine’s. She’ll know you did it for her and appreciate it

Enjoy! I hope you have a great Valentine’s Day. And whatever happens, it can’t possibly be worse than what happened to the real Saint Valentine.

Nick Savoy is the founder of Love Systems and a regular contributor to Playboy. He has an ambivalent relationship toward Valentine’s Day.


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