Relationship & Dating Advice

Dating your ex-girlfriend's sister?

"I broke up with my (ex-)girlfriend a while ago, and we're still friends... recently I'm finding myself attracted to her sister. Is it O.K. to ask her out, since I'm broken up with the ex? Or is that just plain weird?"
-Perplexed in Philadelphia

Michelle: Definitely not a good idea. Even if the sister is attracted to you as well, she won't go for it out of respect for your ex. If she does go for it, you'll cause a catfight between the two sisters.

Adrian: ...which might be cool to watch if the two sisters are hot. I don't know that I necessarily agree with Michelle; it's not an always-or-never situation. It might not be wise given that its only been a couple of months, but is the sister attracted to you? Is your ex seeing someone else? Did you sleep with your ex? There's all kinds of factors that, if you put them together, would help you figure out if it's a safe move or if you'll get a glass thrown at you.

Michelle: Just because Adrian wants to date his ex-girlfriend's sister, doesn't mean that you should try it too. (A cabinet's worth of glasses would be thrown in that case...) If you value your friendship with your ex, don't do it. Otherwise, you should talk it over with your ex first to see if it's cool with her. She may be okay with it, but chances are she'll be hurt by you even asking about it. Just remember that in the end, sisters will stick together, because who else does a girl have to go shoe shopping with? Mmmmm, shoes.

Adrian: Sisters stick together? Come on, your sister got you discounts at Payless! Perplexed, think about how your ex -- and her sister -- will react. You could wind up hurting one and alienating the other. Your odds aren't very good, so be careful not to damage friendships if you don't have to.



NOTE: THE ADVICE IN THIS ARTICLE IS NOT PROVIDED BY A LICENSED PROFESSIONAL, RELATIONSHIP COUNSELOR OR MENTAL HEALTH PROFESSIONAL, AND IS MEANT FOR ENTERTAINMENT PURPOSES ONLY.


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