Dating a roommate

Visitor's Question from a 21-30 year old Male
One of my best friends younger sisters moved into my house I've lived in for the past three years with another of my best friends. She is four years younger than me and I've always found her attractive. My other roommate now has a girlfriend so most of the time it is myself and her hanging out together. We were never really that close before but now every night we would go out she will text me and ask me what I am doing, I've tried to be respectful and realize she is my roommate and not push limits. However, I can't fight the feelings that I think I am falling for her.

After my other roommate goes to bed we usually spend the next hour up together talking until I need to go to bed. Naturally my question would be how to go about taking this to the next level since we already do meals and are always hanging out, but there is another issue. We have a mutual friend who is a womanizer to put it best. If we go out he will look for a girl to take home and if he can't find one he will settle on my roommate and she has had a crush on him and has hooked up with him before. The next day is filled with regret for her usually with her sister, who lives with this guy, at my house about how she wished she didn't hook up with him. it's just an odd situation where I want to date this really cool girl who happens to be one of my best friends sisters, lives with me, and is younger and tends to make mistakes that she regrets.

I think patience will work this out and the more time we spend together the better chance I have.

I guess my question where do you think I should go? I know the general advice is don't date your roommate but there is much more to it and I'm willing to put it all on the line for her. Advice
There definitely are many challenges involved in dating a roommate, but as long as you're aware of them and willing to deal with the fallout, then it certainly sounds like it's worth the risk. Really, the main down side is if it all goes disastrously wrong you have to find a new place to live (or she does) but that's certainly not the end of the world. Life will go on.

So I would start doing those various things that tend to build intimacy. Watch movies together. Go out to dinner together. Go out to a museum, go out to a park, go out skiing or skating or so on. Give her a hug good-night if you don't already. Build up that contact slowly and steadily. When you're comfortable with hugs, add a soft kiss on the cheek.

Good luck!

-- from Lisa
One of Your Friendly Advisors at

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