If you’re like me, Valentine’s Day can be pretty annoying. If you’re in a relationship, the media – and advertisers! – will try to persuade your wife or girlfriend to expect fairy-tale romance. If you’re single, women will wonder why you don’t have a girlfriend.
But that's okay. We're going to use Valentine's Day to our advantage, whether you're casually dating someone or completely single.
If you’ve gone on more than one or two dates with a woman but she’s not your girlfriend, Valentine’s Day is a bear trap waiting to be sprung. If you try to spend time with her on Valentine’s Day, she might get turned off and think that you’re pushy or smothering or not much of a challenge. If you don’t spend time with her on Valentine’s, you risk her friends texting her stuff like in the picture below, or convincing her that you’re not worth it.
Her reaction will tell you a lot. She definitely knows that Sunday is Valentine’s Day. If she implies she is busy or has plans, drop it. Further probing will make her feel that you are more interested in her than she is in you, which is a great way to kill attraction early on. But if she leaves it open, you should say something like “cool, we should do something” – and leave it at that.The solution depends on what you want. If you want to advance the relationship, Valentine’s Day can be a very useful tool, if you use it correctly. Don’t ask “do you want to go out with me on Valentine’s Day?” – that will remind her of high school nerds who used to screw up their courage to ask her to the prom. Instead, test the ground first. You can do this by relying on the stereotype that men are clueless at romance. This year, Valentine’s Day is on a Sunday. So, up to a week before, you can ask her casually what she’s doing ‘next weekend’ – in the same tone that you’d use to ask about any other weekend.
One mistake I've seen guys make with this is that get specific about Valentine's. You don't want to have a dialogue like this:
YOU: So, what are you up to next weekend?
HER: Not really sure. No plans at the moment.
YOU [BAD]: Cool, let's do something on Valentine's Day
YOU [ALSO BAD]: Cool, let's do something on Sunday
YOU [GOOD]: Cool, we should do something
(And if you’re wondering, it’s not that bad if by being ambiguous, you end up seeing her Saturday night instead of Sunday. When Valentine’s Day falls on a Sunday, a Saturday night date “counts.” This is one of those rare years where you really could get away with having two separate Valentine’s Days with two different women, which is fine if that’s your thing and you don’t have to lie about it).
If you’re completely single, do not desperately try to set up a Valentine’s Day date. Don’t put yourself through an all-night tinder marathon or start desperately combing your friends-of-friends on Facebook. Any first date invitations for Valentine’s Day (even if you pretend not to know that it’s Valentine’s) will make you seem try-hard, even if she is as single as you. Even if she says “yes,” the actual date is likely to be awkward as heck.
Instead, go out. Grab a friend or two and go to your nearest bar (or mall or coffee shop if you're a day game guy). Single women will be out on Valentine's Day, but you need to know what to do.
Typically, when single women go out on Valentine’s Day, it’s with their single girlfriends and it’s usually framed as a “to heck with guys, men suck, we’re going out to have fun!” So her friends might see her as letting the team down a bit if she is distracted by men like yourself instead of her focusing on her single girlfriends. And because Valentine’s Day is going to bring out more jaded and bitter behavior from single women than normal, be prepared to handle her tests, like "why don't you have a girlfriend?" or "why don't you have a date tonight?"
Yes, I know. The woman asking you clearly doesn’t have a boyfriend or a date either, but responding logically isn’t going to help you here. The best way to handle ‘tests’ like this is usually to exaggerate them to absurdity and then turn them into a joke. For example:
"Why don't you have a girlfriend?"
"I actually have 8 girlfriends. That's my limit, but I'm thinking of replacing #6. Normally new girls have to start at the bottom but if you play you cards right you might just be able to grab that 6-spot."
"Because I just met you, silly. Buy me a drink first."
"I thought we were supposed to leave boyfriends and girlfriends at home. This is the Ashley Madison Valentine's Day meetup group, right?"
"I traded her for a camel." (pull out your phone and start showing her pictures of camels)
Be prepared for a lot of attitude at first, but know that if she’s single and out on Valentine’s Day, she wants to meet a cool guy. She just has it in her head that most of the single guys out on Valentine’s are guys she needs to weed out. Once you show her you’re one of the cool ones, the rest of the road should be a lot easier.
Let me know how it works out for you in the comments!