Is he interested or just bored?

Hi Ladies,

Thanks for reading this in advance, I’m just a confused mess. So this guy I have gone a few dates with, we have a complicated origin story. We met on Tinder around May. Hit it off, he made plans to go to this local bar, we had fun, we were obviously attracted to each other. We took a walk around and made out a little. He invited me home and I declined. He contacts me for a second date, another bar in his neighborhood. We were in the bar maybe 20 min before I demanded he take me to his place. We had amazing sex, however the condom broke. Grabbed a plan B and we texted a little after that. But we couldn’t make plans because his family was in town, and then I was away on vacation, then he was away on vacation and we lost contact. I really liked him beyond the sex and was a little insecure maybe that was all he was interested in, so I didn’t really try to pursue him, and he didn’t really pursue me either.

Then a couple months later, after a night with the girls I send him a drunk text asking him what he’s up to. He replies that we should hook up again soon, and I thought all my insecurities were validated. I never responded.

Fast forward 5 months, and I see his profile on Okcupid. I press the like button because fuck it, curiosity. And it shows we match. That night he messages me. We have awkward small talk and I tell him if you wanna see me, text me when your free. 2 days pass. I visit his page again, and within that night he texts me asking when I am free. We go out that wednesday and have a great time. I remember why I liked him so much to begin with and we go back to his place too fool around. No sex though, and I don’t spend the night, cuz feelings. And I text him a couple of days later asking when I can see him again. He immediately responds with dates that are good for him, and we go out to a movie. He is a complete gentleman. He holds my hand, tells me how pretty I am, and he generally is really digging me. Everything is now sweet, there less sexual tension. The way he holds me is softer. He tells me after the movie he has work very early in the morning so I can’t come over, but he has time for one more drink. I can see him slowly getting more and more tired so we grab the bill and head out. We chat while locked in each others arms on the train. I kiss him goodbye and he gets off. We had made tentative plans that we would see each other that following sunday. Saturday day I text him to see if we’re still on. He says He’ll text me in the morning. Sunday afternoon he texts that he had rough night, and he’s not really up to company today. I totally get it. Hangovers and dates don’t go well. He says we’ll see each other soon though. See. This is my problem. I have initiated contact first. Every time. Even if we was the one to “make the plan” it’s cuz I texted him first with whatever banter or something. He never texts to see how my day is going or anything. And it has been days since we last texted. I want to text him and make plans because I want to see him. But shouldn’t he text me if he also wanted to see me?

So my reasoning is this: either he isn’t that interested but just bored. When I remind him I exist he is down to hang out, but he never actively seeks me out. Or he has picked up on my insecure vibes and he isn’t sure if I actually like him (i.e. he says you’ll meet my boss sooner or later, and I never say anything like that). So help a lady out. Because I do really like him, but I am not down for wasting my time.