Josh Sway
JoshSway.com is every man's source for dating, relationships, self-improvement, and more.

Articles advice from Josh

/ What Should You Do On Valentines Day?

Not sure what to do tonight? Here is some advice!


This Friday, it’s Valentine’s Day, which means you have a choice. You can choose to sulk in your loneliness and grump about everyone to shoving their affection for each other in your face. OR, regardless of your situation, you can take advantage of a fantastic opportunity to meet someone new, or escalate things to a new level with a girl you’re already interested in. I strongly recommend you choose the latter.

See, contrary to most guys’ opinions, I actually love Valentine’s Day. Valentine’s Day, more than any other holiday, presents an opportunity for an amplification effect on women for pretty much anything you can do. Your actions can generate attraction much faster than if you did those same things on any other day. Of course, this is a double-edged sword, and many guys have found their romantic gestures totally backfire because they came on way too strong. But the good news is, you don’t have to be one of those guys.

Read below, find what situation most describes your current love life, and read my advice on what you should do tonight.

If You Want to Meet Someone New

Go out! Especially since it’s a Friday. Hit up a couple of your guy friends and go find a cool party or go out to a fun bar. Wherever you go, you can be sure that every single girl there is single, because all the girls in a relationship are already out with their boyfriends. There’s a reason why people say "hitting on girls on Valentine’s Day is like fishing with dynamite."

Whatever pain loneliness brings, Valentine’s Day makes it that much more acute for everyone. Every girl out on Valentine’s Day is really just looking for a way to stave off that feeling for a couple hours until it can become bearable again. Try lots of openers and you’ll find girls will be much more receptive because you’re giving them companionship, even for a few brief moments. Leverage that opening to build attraction and escalate in situations where you’d normally get shot down right off the bat. And Valentine’s Day itself provides lots of great opportunities for situational openers related to V-day.

You Think She’s Interested, But You Haven’t Gone Out Yet

Maybe you got her number last weekend, or she’s someone you recently met in class or at work. You’ve texted a few times, she seems interested, but you’re wondering whether going out on Valentine’s Day will "send the wrong message." Many guys think going out on a first date on Valentine’s Day is a bad idea, but that’s only true if you get sucked into doing the Annoying Expensive Dinner.

So, don’t do that. Your best strategy is to basically pretend it’s not even Valentine’s Day. If you’re over 21, ask her if she’s free to have a drink on Friday, just like you’d do if this Friday was any other day but Valentine’s Day. Ideally, she’ll jump at the chance of companionship you’re offering her.

Suggest going out to drinks at any place that’s not also a restaurant, because you want the fact that it’s Valentine’s Day to just kind of lurk in the background and not be shoved in your face or hers. Have a few drinks, and then at some point in the night when you feel the moment is right, kiss her. Then say, "Happy Valentine’s Day." If you do all of the above correctly, this should be the easiest escalation of your entire life!

You’ve Been Out A Couple Times

So you’ve been out a couple times with this girl, you like her, and you want to escalate without overcommitting. You’re walking a very fine line here. This is the only situation that I may recommend just being unavailable. If she drops hints she wants to do something, just tell her you’re busy and you have to see your family or go out of town or something. In this situation it’s really easy to fuck it up in either direction. Come on too strong, and you may end up making her think you want to be exclusive way sooner than you want to, or freak her out because she thinks you’re moving too fast.

However, if you can thread the needle, this could be fertile ground for escalation. Find some reason to occupy yourself for most of Friday night — for example, say your friend is in a band and has a gig and you said you’d help him set up. Then ask her what she’s doing. She’ll probably have some plans to hang out with her other female friends, probably some sort of "girls’ night," which is ideal for you.

Then at some point on that evening, tell her you got out of your commitment early, and you’re now free and ask what she’s up to. Offer to have her come by your place, or for you to meet up with her. If she’s spent the night stewing with her female friends and lamenting their loneliness, she’ll eagerly take you up on your offer of companionship. You’ll look considerate for getting out of your commitment early to see her, and she’ll be so happy to have some companionship she won’t care that you didn’t get her a bunch of flowers and chocolates.

You’re Seeing Each Other Regularly

Well, you probably have to do something, so just avoid the Annoying Expensive Dinner, since it’s, well, annoying and expensive. If either of you have any ability in the kitchen at all, I recommend you suggest you go out, buy groceries, and cook dinner together. Way less annoying, way less expensive, way less dramatic, and way more fun. This way you can control the romantic mood as much as you want it to. You can keep it casual and just cook a basic meal, or go all out with three courses and candles and wine and music. At least it’s in your control, and you don’t have some restaurant shoving all of that in your face.





If you've enjoyed the articles on JoshSway.com, there's even more advice in our e-books!

Buy Now!