Q: I've been hanging out with this guy since school started. We've hooked up a few times, and he calls me every time he goes out and asks me to join. The only problem is: we've never hung out sober. How do I turn this drunken fling into something more meaningful?
A: Straight up, the first thing you need to figure out is whether he’s genuinely interested or just trying to get some play. Very often, the I-only-call-you-when-I’m-drunk-and-lonely situation is nothing more than, well, a booty call.
However, in my opinion, any guy interested in your hook-up should be interested in your “hang out” as well.
Assuming that his intentions are worthy, it is quite possible that he’s also unsure how to take your little fling to the next level. Your mission: take matters into your own hands and make the first move
Next time you go out together, send him a Facebook or text message the next day, when you’re (hopefully) sober. Your message could go something like this: Hey (shy guy), just wanted to tell you that I had a lot of fun last night. My schedule is kind of crazy this week, but I was thinking we could meet up for lunch one day. Got to eat at some point, right? —(dream girl).
In your note, be confident and cool, and take a simple and straightforward approach. You don’t want to come off as snobby or insecure, but you also don’t want to make yourself seem too available — a short chase around the block is fun, but at this point, asking him to run a marathon is unnecessary.
You’ve hooked up on multiple occasions, and he still calls. If he responds to your message and wants to set a date, take it as a sign that he’s super-relieved that you took the initiative and made the first move.
If he ignores your message but then calls the next weekend, do yourself a favor and raise your standards. Even in the age of Facebook and text messages, actions still speak louder than words.
If he deserves your heart, he’ll find a way to win it over on his own, without his loyal companion Jack Daniel holding his hand.



