Should I Hang Out With Him?

Nick Slade Nick Slade • 9/25/14

Reader Question:

In high school I had a crush on this guy. Lets call him Fred. My friends told Fred that I liked him and long story short he liked me, too. He asked me to prom, and I was SOOO happy.

But later on, I didn’t want to go to prom with him. It wasn’t anything personal. I just wanted to go by myself. There was also a bit of peer pressure because all of my friends hated him. I was a little bit of a jerk to him, and I’m totally regretting it now.

To my surprise, he later sends me a friend request on Facebook. Then I realized I still had feelings for him and got in touch with him. I hinted that I wanted to hang out with him, and he asked me if I wanted to hang out with him. (HUGE RELIEF!)

We watched a movie and held hands nearly the entire time. After that, I had to initiate conversations. I asked him if he wanted to hang out again, and he said he’d have to find some time as he was very, very busy.

However,  we still text each other. Sometimes he would take FOREVER to respond to a text. I later got over him, and I would blow him off because of how he blew me off when he was SO “busy.” I let him know that this is his last chance because of how he blew me off. He tells me that he was so busy that there were moments when he could “barely eat or sleep.”

We eventually hang out a second time, and he hugs me while the movie is on. The movie ends, we talk a little and he leaves.

Some months pass and he asks me to hang out with him, and I blow him off this time because he takes too long to reply. Yet, he still continues to ask. On some rare occasions he even calls me. I give in and the whole time before he came over, I was certain I was over him and that this wouldn’t bother me. But I have so much fun with him.

While we were watching TV, he would put his arm around my shoulder and would lock his hand on my wrist when I would try to get away. I always tell him he has to leave before my parents get home. I don’t want my parents to interrogate him and he knows this. He has asked me, “How many people have been interrogated?” Am I wrong to think that he’s asking how many guys have met my parents?

I text him the next day and we had a small conversation. I REALLY wanted to hang out with him again, but I didn’t ask and neither did he. Also, after our whole prom debacle, I feel like I don’t have the right to ask him, and all we do is watch a movie or TV at my place, so I don’t want to bore him.

I would really like to know if you think he likes me, if you think I should hang out with him more and tell him how I feel, or if I’ve caused him enough trouble already and should just leave it alone. PLEASE HELP!

-Carmen F. (Maryland)

Expert’s Answer:

Carmen, Carmen, Carmen… NO! You should NOT hang out with him. You should DATE him! That would straighten out a lot of the confusion for both of you, as far as what kind of relationship you have. You are both treating this like some kind of third grade play date, while the unrequited sexual tension just “hangs out” until it finally evaporates, only to return again next time.

It’s time to take this to a more adult level and explore the possibilities. You’re obviously infatuated with each other, but there are some hard feelings and trust issues.  There is no grown-up willing to be the first one to extend a little trust and vulnerability because of the game of “jilt tag” you’ve been playing with each other for so long.

Here’s what I would do (if I were a young woman):

Call him on the phone. Leave your third grade alter ego at the playground, and make a business call. Tell him you have something important to talk about and you want to schedule an hour for coffee. Give him two dates and times to pick from, and if he plays the “busy” game, tell him to break one of his appointments because you really have to do this. If he wants to know what’s so important, tell him he is. No more. You’ll discuss the rest in person, or you won’t discuss it at all. If he says no, he’ll call you back in a day or two.

When you’re face to face across the table, do a little catch-up small talk and then look at him. Pause. Begin with something like:

First of all, you know it was a long time ago, but you want to tell him that you are sincerely sorry for breaking the prom date. You feel like this mistake is always hanging over your head and gets in the way of moving your friendship forward. You were a jerk, and you’ve felt horrible about it for a long time. You were a kid, and the other girls all wanted to go together with just the girls. You were really excited about going with him, but you caved to the pressure. You were wrong to break the date, you deeply regret it, and you can’t live with the guilt any longer. You want to ask him to please forgive you.

Stop. Look at him. Wait. There may be a long pause, but the next words have to be his.

He may tell you how bad it made him feel. He may lay it on you hard, and he may even cry. Who knows. Take his hand, look him in the eye, and ask for forgiveness again.

Next, tell him you want to figure out what kind of thing you have going with each other now. Ask him if he felt like the times you were together were dates. Tell him there were a lot of times that you were hoping he would kiss you. Tell him you understand if he held back because of the horrible thing you had done, but you would like to get past all of the hard feelings and the weeks between responses.

Ask him if he enjoyed the times you’ve spent together. Tell him that you’re both grown-ups now, and this relationship can’t keep going the way it has been.

Tell him you value his friendship and sometimes you see possibilities for more, but you’re just confused and can’t tell what he thinks about you for sure. Ask him if the two of you should try a real date. Then make plans to actually go OUT on a real date. Give him a hug and a little kiss, and thank him for coming. Tell him you feel so much better now. Let him know you’re excited about your date — and you won’t break it!