Should I date this guy?

Okay, there is this guy, we've been friends since high school and recently, I've been talking to him, we're not really in a relationship, but he says that he likes me and I kind of like him too. There is one thing though, he's always telling me that I'm sexy as hell and he even once asked me to email him pictures of me in lingerie and bikinis, which is kind of strange to me because 1) I'm plus size and 2) all my life, guys have always bullied me, made fun of me, and told me that I was ugly, so I've never had a boyfriend. (I haven't emailed any pictures like that to him though.)Also, he's told me before that he would really like to show me what other guys should have shown me but never had. What I want to know is if I should date this guy or not.


Most Helpful Girl

  • I don't think there is any harm in dating this guy, he wouldn't be chasing you if he didn't like you but what I would say is don't send him any pics if your not comfortable with this, especially as you aren't dating. I have been seeing a guy for a month and he's always asking for pics but I've told him I'm not comfortable with it and he's fine with it. I did send him a jokey one in my bikini but I covered my face, he had seen this pic before on my social networking site though. Go on a date with him, get to know him more and have fun. Just because you are a bit bigger and were bullied doesn't mean you can't find a nice boyfriend. On the conterary of what people think there are some decent guys out there. I hope this helps.


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  • I think he is coming on strong in the sex department and it isn't the greatest thing that he is asking you to send him pics in lingerie and a bikini. So, I would tread carefully. 1) Once you take a friendship to the next level, you can never go back to friendship. It just doesn't work, so you risk losing him as a friend if things don't work out. 2) You would want him to become a boyfriend and he is focusing on sex right now, from what you present here. You will have to make it clear if you start dating, that you want time to get to know each other and you are not ready to jump into sex. You need to date him a while and see if he is focusing energy on knowing you as a whole person and respecting you before you jump in to sex.

    Women of all shapes and sizes are sexy. Guys are not all looking for one-size-fits-all. There are guys who specifically love a full figured woman. Love it. I would just take care so that you don't end up rushing into this and have your heart broken if he was looking more for a fling than a relationship.