I'm a 30-year-old gay guy living in Brooklyn. I've been dating this guy for about six weeks now. I really like him, and enjoy spending time with him. At this point we hang out about once a week—we both have full time jobs; he lives all the way up in Harlem and I'm a single dad to a dog in Brooklyn. The problem is that every time we hang out I have to initiate, I'm always the one asking him out and making the plans. When I do this he's pretty much always available and down to do whatever it is that I'm suggesting. I've brought this up to him, sort of in jest, but thought he would get the hint. He then immediately asked me out to dinner when he knew I'd be busy. He was obviously joking around and was fake-crushed when I "rejected" his invitation. Like an idiot I asked him out twice more after this little conversation, once to a Cinco De Mayo party, and then a few days later to see The Normal Heart. We haven't seen eachother in almost a week, but have been texting.
He's going away on business this weekend, but when he comes back I'm not going to be the one to initiate plans. Do I not do anything and let the relationship fizzle out? I was thinking of saying something again, but sort of feel as though asking him to ask me out is still asking him out. What should I do?
Wanna Be Asked
My response after the jump...
Stop playing games, stop dropping hints—and stop being such an insecure, reciprocity-obsessed fag about this, WBA.
If you really like him and enjoy spending time with him and want to keep seeing him, then keep asking him out. If having to do all of the asking out makes you feel unwanted or unspesh, WBA, don't bring it up "sort of in jest" and then get all buttsore when he responds to your sort-of-in-jest suggestion with a jesting-back-at-you invitation. Tell him straight up, in all seriousness, that it's hugely important to you that he make the plans and extend the invitations now and then.
If he comes through with an invite or two, great. If he doesn't but is always available when you call, WBA, then you just might have to accept that this guy likes you—really likes you—but isn't the plan-making, invitation-extending type. You can choose to view this as a negative ("He doesn't care enough about meeeeeeeee to ask meeeeeeeee out!"), WBA, or you can choose to view it as a positive ("I enjoy making plans, he enjoys having his plans made for him; I'm the invite top, he's the invite bottom. I would prefer to be with someone invite versatile but, hey, you go to The Normal Heart with the boyfriend you have, not the boyfriend you might wish to have.").
In other words, WBA, the dynamic that's troubling you could be evidence that this relationship is doomed or it could be evidence that you two are actually kinda compatible. You'll have to stick around—and keep invite topping the shit out of him—to find out which one it is.
