So, I've noticed this trend in my relationships (kind of a grand word for them!), and when I thought about it, I noticed it in my friendships too. Like a lot of folks here, I've struggled with depression. I'm doing better now (career change, lifestyle change, a huge health scare that I think really shook some sense into me about a few things). I've lost more than a hundred pounds (still a ways to go, but a huge improvement), no longer work 80 hours a week, go to the gym regularly, and stuff like that. However, despite these improvements, I'm still massively insecure about myself. Physical appearance, but also that people will think I'm boring/not fun to be around, etc. With friendships, this manifests itself in buying small gifts and doing small favours for folks (tickets to shows, rounds of drinks in bars, gifts). A few of my friends have called me on it - they say I'm paying for things to get people to spend time with me (which is absolutely true), and despite their insistence that it's unnecessary and that they want to hang out with me anyways, I still keep doing it. In romantic relationships, it's BIG gifts and BIG favours - the same problem but much more compounded. A straight guy I had a huge crush on, I bought him an insane amount of stuff (including a flight for him to visit his girlfriend - I know, it was a really great plan. Yeesh.) For a guy I liked earlier in the year, I arranged for him to get sponsored to a conference (flight, hotel, registration fee). And most recently, with a guy I had spent a few nights with when he was visiting Calgary (met off of a rather famous gay pick-up app), I booked a freaking trip to see him in Atlanta, paid for a hotel for four nights, and paid for meals, drinks, and the rest. In the case of the romantic relationships (or at least where I like the guy), I seem to just jump headlong and make really bad decisions. I think what's happening is that because I'm insecure about myself, I have this subconscious conversation which goes something like: "I can't believe this guy likes me - he'll probably come to his sense soon - I know, I'll buy him a bunch of stuff to make him like me", or something like that. I just seem to have a real problem breaking this habit - and I'm really certain it comes down to self esteem. The thing is, apart from being a bit over-weight, I think I actually have pretty decent qualities. I'm nice, funny, smart, hard-working (please excuse this self-promotion) - my point is, I can't really figure out where this personal insecurity comes from. Is it residual feelings of shame for being gay (which intellectually I know was in no way a conscious choice, although emotionally I'm still struggling with still here and there), or a hold-over from when I was really over-weight and I still see myself through those glasses? Has anyone else here encountered this situation or adopted similar behaviour? And more broadly, what have people tried (and found has worked) in feeling better about themselves?
