Dear Sugar,

I just got out of a relationship over the Summer, and I finally feel like I'm ready to move on. There's this guy I've been interested in for a while now who I've known for almost two years. I realized not too long ago that I might be falling for him, but there are issues getting in the way of me taking a chance. The first thing is the guy I like is best friends with one of my family members, and I don't know if he'd mind me dating one of his friends. I also don't know how to bring it up to my family member, since he's a guy and it's hard for him to understand girls. And the other problem is that whenever I'm around the guy I like, I get so nervous. When I try to talk to him, I freeze and just smile. What would you do if you were in my shoes?

—Out of Ideas Ida

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Dear Out of Ideas Ida,

So it's great that you feel ready to get back into dating. I can understand you're feeling nervous and shy around the guy you like, but just try to be yourself. I know you like this guy, but I'm wondering: Do you get the vibe that he likes you too? Does he flirt or try to talk to you when you see him? If so, it might make you feel better to realize that he's probably nervous to talk to you too.

If you're not sure what he's thinking, I'd be patient and feel out this situation. You don't want to proclaim that you like him, because if by chance he doesn't feel the same, it would break your heart and make things really awkward between you.

If you do get the feeling that he's into you, then I'd talk to your family member. It's really considerate of you to respect his feelings first. Don't make a big deal about it — just be upfront and say, "I like your friend and would like to try dating him. Would that be OK with you?" Since he's friends with the guy, I'm sure he'd be psyched about it. He could even help to arrange for you guys to casually meet up. This all sounds so exciting. I hope things work out for you two.

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