Some background info about me. I am in my late 20s, have dated, I have been in several serious relationships, and a short marriage that lasted 2 years. I have been dating for a year now, and I want to get married again, or at least have a serious lifelong relationship with someone. I know, I just haven't learned my lesson, yet.
I went on a date with a woman who I met online. Okay, it wasn't a date... we had talked a lot on the phone and through text, and we had a date arranged, but we rushed it and she invited me over to her apartment to hook up. When I met her, she looked like her pictures, except that she weighs like 30 or 40 lbs more than I thought she did, which is quite overweight (not quite obese). For me, it is a problem because I have never been attracted to someone with a weight problem. Looking back, I don't think she was trying to mislead me. I think she is insecure about her body image. She called me out on my thoughts right away that night, and I had trouble being honest with her about that bothering me - I didn't want to be a total jackass. I eventually told her, in the most tactful way that I could manage. She said she was not hurt by me being honest and she knows she has a problem. According to her, she had to go on a medication for severe allergies that caused her to start gaining weight. She was on it for a year, and she said she had gained 20 lbs. Before that, I think she was 120 lbs or so, and she is 5'1.
To backtrack a little, talking to this girl, I feel like I have found the person who is closest to me personality-wise that I will ever meet. We have almost everything in common, from weird picky food preferences to music to random personality quirks that I have never shared with anybody. She has shown me full-body pictures of herself from a few years ago, and she is beautiful in them, like super model beautiful. She has a very pretty face - even now. It does seem like the weight gain is from a medication.
She told me she has always been very conscious about her looks and is very insecure and uncomfortable about the weight she has put on, and by November this year, she would like to lose about 40 lbs. She says she eats very healthy (always has) and is dieting. She says she hasn't exercised much, and has never been a very athletic person, but that she plans to. It seems like an attainable goal. I think I would like to wait it out and see it through because if she lost the weight, she would be everything I have ever wanted in a woman. I am just worried about problems we would face in the long run - I don't know how I would be able to have sex with her until she loses some weight because it is a turn-off. This might be too explicit for this section of the forum, but the hookup we had was kind of awkward. I could not maintain an erection and ended up getting frustrated. She was very good - the best I have ever had - in the oral department, though.
I just need to hear some third party's opinion on whether or not this is a good idea.