I met a girl on a dating site after being single for a while(I've only really had one serious girlfriend before, but it lasted a while). I spent the weekend with her last week after video chatting/talking on the phone with her for about a week and it went well. We ended up having sex a few times and she wants to come back this weekend(I work during the week and she lives a town away, but it's only a half hour bus ride).

I'm not sure what to do next. She was a sweet girl and it was nice to have someone next to me in bed to cuddle and spend time with. She seems to want a relationship and I do as well to a point. There are a few issues that are troubling me - She has never had a job(she's 23) and has a caregiver(??) that she and her mom live with but she wants to move out soon after she gets a job. She also has to take medication(vitamins and bi-polar though she says it's not major) seemingly everyday. She is a bigger girl though, but a very cute face and personality. I've seen pictures of her when she was a few years younger and she looked amazing so I know that if she lost a few pounds she'd be perfect but that's making me feel like an ass which is part of the problem I'm having.

She's not really a girl I feel comfortable bragging about or bringing around friends at parties. I'm a shy person and have trouble being myself around very attractive girls. I'm a fairly decent looking guy, but I'm also not in the best shape at the moment(I could lose about 25 lbs and be good). I'm being shallow, but I do really like this girl and want to spend more time with her. Should I just take it slow and test the waters for a while?

Has anyone ever dated someone who had to take medication or someone who lived with a care giver? What does that even mean? She said she was in a foster home since 14 and her mom's on disability. Her caregiver seems like a task master from what I heard on the phone when she called and from what I've been told. Anyway, I just hastily typed this up and any insight would be appreciated. Thanks.