[clacker80]

I’ve been friends with this girl (who I’ll call Lisa) for close to 15 years, I met her through my ex-girlfriend (who I’ll call Kim) who I broke up with over 10 years ago.

After a few months of being apart I started talking to Kim again and we decided we were better friends then lovers, so for the past 10 years we’ve hung out as friends only and have dated other people here and there. I’ve always liked her friend, Lisa and never mentioned it to either of them before. But I really would like to date Lisa now. Lisa says she won’t date any of her friend’s ex-bfs because that’s against “girl” rules…. plus Lisa did date one of her friend’s exes and things turned out badly.

I really would like to start hanging out with Lisa just us 2. For the last 15 years since I met her we never hung out alone there’s always been other mutual friends with us. But it would be nice to go out on a date with her, the only thing is I don’t want to ruin our friendship. And I’m 99% sure if I was to even ask her out she would get pissed and/or scared and that would ruin our friendship altogether.

Does anyone have any suggestions on how I can approach Lisa and not freak her out or ruin our friendship?

[April Masini, your AskApril]

Whenever you date a friend you run the risk of an upset in the relationship, however, if the friendship was strong to begin with, it will sustain bumps in the road. However, if you’re 99% sure, already, that asking her out is going to ruin the friendship, the risk is pretty clear.

The question for you is is this woman a potential Ms. Right or are you just bored and she’s an easy mark? If you really think that she’s someone you might want to spend the rest of your life with, then you should take the risk, but if she’s just someone else to date, it’s probably better to look elsewhere.

I hope that helps. Let me know how it goes!

Please follow me @AskAprilcom on Twitter and on Facebook at this link: [url][/url]

[Member]

Posts