Then Jack Happened


Dear Jack:

I’m having a problem with a guy that I am ‘dating.’  We met on an app a few months ago. We were texting and having a good time and getting to know each other. We planned on a date but I got real sick and was MIA for a while so we fell out of contact for a couple months. We got back in contact eventually and finally went out. We went to dinner and I definitely got a romantic vibe. We were out and I told him that my family was at a nearby restaurant having drinks. He told me he could drop me off. I invited him to the bar and he met everyone and my dad, who is a really outgoing guy, invited him over for a night cap. The guy accepted and we ended up hanging out at my parents’ house for a couple more hours. Since then, we’ve gone out several times but he hasn’t made any romantic moves. We have a great time, it seems flirty, but in the end nothing.  I think it has something to do with my family. I am interested in him as more than a friend, what should I do?

Make your move! Maybe you wait when the time is right and go in for a sloppy wet one. Maybe you sit him down after a nice date and ask him, “What the hell is going on here? You know I like you right?” But however you play it, you won’t get to the bottom of it until you, or he, makes a move.

My first reaction was that he isn’t romantically interested. I don’t have a very high opinion of us guys and assume a lack of aggressiveness, particularly when we are talking carnally, indicates a lack of interest. But, then I got to thinking, maybe you found yourself a nice guy! They’re real right? He waited out your illness, hung out with your family (on a first date!) when he didn’t have to, and he’s spent a lot of time getting to know you. Now you’re waiting for him to make him a move, but maybe he’s not the sort to take the bull by the horns. Maybe that means he isn’t the sort for you. But if he is the right ‘sort’ despite the difference, then it might be time to ‘re-sort’ yourself and be the aggressor.

We don’t have enough information to determine if your family is the problem. The evening sounded fun, if not a bit quick. Maybe the transition from romantic date to comfortable family situation signaled that you were the one not romantically interested. Maybe your dad threatened him. Maybe he’s looking to be adopted. And maybe on and on until we get some answers.

Which means, it’s communication time! Look, I get it. Rejections sucks, but this has gone on long enough without answers and at this point, what do you have to lose? If he’s into you then it’s magic and romance, if he’s not, time to move on or keep the friendship. It can be scary initiating these conversations, but you will feel relieved to get it over with and I can’t imagine that he doesn’t have some of the same questions and will likely be relieved as well. Nothing risked, nothing rewarded, now go get you a man!

Del Ray, get over here, this has gone on long enough, give me your hand, look in my eyes, tonsil hockey until you send all your problems to