Please Advise: How many boring dates should I sit through before I cut and run?

Pin it

How many second chances should an attractive guy get?

Leslie Kwon

Wise readers, 

Each week, the inbox of our venerable advice columnist, Miss Information, is flooded with queries. And although she makes a valiant effort, she cannot answer them all. To deal with the surplus, we've decided to turn to you. So, don your spectacles and help this woman out. You can give her advice in the comments below, or, if you'd like to share what you wrote with your friends, on our Facebook page. 


Hello Nerve!

I'm a woman in my twenties, and I've been (sort of) dating a guy who's two years younger than me. We've developed our friendship through Facebook — it was a friend-of-a-friend type thing. We have been messaging for about six months. 

A few months ago, we had our first real hang-out. It was awkward. During lunch, he seemed uncomfortable, almost unhappy. Later, we saw a movie, and he went the other way, trying awkwardly to put the moves on me in the theater. I honestly thought the guy was confused about what to do; I didn't feel like he was a jerk or anything.

After a few more weeks of messaging, we met up again, a couple weeks back. The delay, I think, partly comes from the fact that he's super busy; he works full-time, plus a side job and is a part-time student. This time was much better: I had fun and felt more comfortable talking to him than before. We left things with a plan to meet up again, but didn't set a time or place.

Basically, things are moving glacially. My friends think I am wasting my time, that the guy is playing a game of hot-and-cold. He says things that indicate he's interested, but then doesn't put in the effort to make things go further. I don't think we need to be constantly communicating, but I do believe that, if he was really smitten, he'd be doing a lot more than casually messaging every once and a while. 

Regardless, I'm still attracted and interested in discovering more about this guy. I do want to see what's going on with him and would like for it to go further, without me being pushy and of course, without getting hurt. So what do you think? Is he interested and maybe just has no idea how to romance girls? Or should I cut and run? 

I need your help!

— Hot & Cold