Dating 101 (Part 2)

Step 4: Take the plunge

Gage the situation, and eventually, ask her out. Preferably in person. This is scary, but it’s mainly for your benefit. I’m just watching out for you, man. You’re going to want to see her reaction, because you’ll be able to tell if it’s a green light, or a yellow.

…ARG, did you wimp out? Again?! Yeah, I know she’s cute, but hold it together man! OK, you can do it online if you must. Bring up a movie you want to see, or a restaurant you want to try. Ask her if she wants to go. If she says yes, be cautiously excited. She might just be nice, but she wouldn’t see you if she didn’t at least think you were an OK guy, so you’re pretty much in. (If you had asked in person, it would be easier to tell her level of interest, but it’s ok, I understand that there’s a reason you’re still single. OH I kid. You’re awesome. Don’t ever doubt yourself!)

If she says no, take a step back. If she says no, but seems like she’d be willing to go some other time, definitely go for it. Don’t think about it that much, just do it.

Be careful of how you phrase the asking out. The best thing to do online is make it a spontaneous, “Let’s go right now” type of thing. DON’T back her into a corner and ask “When are you free sometime this week so we can go to _____ together?” Doing things online gives her too much time to think, and sometimes… it’s better if she doesn’t have time to think too much.


Step 5: Recovery

At this point, you either got the date, or you didn’t. If you didn’t, she’s probably just not that into you. It’s up to you whether or not you want to continue the friendship.

If, however, you are a stubborn guy, perhaps, well maybe she’s just shy. This is not usually the case, so don’t push it too much, but if you really just HAVE to make sure…

Option 1: Ask her out in a group. Invite her to the bar with you and your friends. Or to a late night showing of a movie you were going to see anyway.

Option 2: Feeling bold? Yeah, you can ask her out again. If there’s another excuse though, with no suggestion of a reschedule, give it up.

Option 3: Study date. Strange that you haven’t asked her to do this before, if the circumstances fit. Just thought I’d throw it out there anyway.

Option 4: Be her friend. This pretty much ensures that you’re never going to get more than a “Aw, you’re an awesome friend!” Hug, but hey, you can dream big, and crazier things than friends hooking up have happened. Just don’t hold your breath. And if you do, be prepared to hold it for a while. Eventually you’ll start hanging out together, but as just friends. Damn. This is pretty much the worst option.


Step 6: Move on

So you tried a couple times, and you could keep trying, but don’t be an idiot. Find another cute girl. Stop seeing this one, even as a friend, if you’re not noticing any other cute girls. There are ALWAYS cute girls, and you are just blinded by your crush. Extract yourself from the situation, gently, because she’ll notice once you stop calling/texting/facebooking/whatever. And then you just come off like a bad friend.

Find someone else, and start all over. Isn’t dating fun?

Cynics say that dating is a numbers game. Don’t be a whore about it, but just know that for every girl your friend nicknamed Casanova banged, there’s a girl out there that rejected him.