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Falling for a Friend's Ex
Should I tell my friend?
Wednesday Apr 26, 2006.     By econfidant
Centerstage Chicago Nightlife City Guide Arts

I finally met someone really cool! Only problem is that she's my friend's ex. I keep running into her and we've been flirting a lot. I don't know how my friend would react. Should I ask her out? Talk to him first?

It is wonderful that you met someone you like, and I can tell you're in a difficult position because of her history. While your concern for your friend's feelings certainly complicates the situation, it also reveals your sense of loyalty and maturity. If you feel an undeniable chemistry and a sense that you will regret not asking her out, then it is probably best to approach your friend before proceeding.

Think of it this way, your alternative is to give-up a possibly great relationship without knowing how your friend would have reacted OR to conceal a relationship from your friend and deal with a confrontation somewhere down the line. If you talk to your friend now, then you give him the chance to react honestly.

When you talk to your friend, start from the beginning. Tell him exactly what you told me- that you have run into his ex frequently, flirted a lot and that you would like to ask her out, but you haven't because you wanted to talk with him first. You can explain that you didn't plan it or that you wish it wasn't his ex, but the news will probably come as a shock to him regardless of how you phrase it.

Listen to your friend's response. Ideally, he may have moved on from the relationship and give you the go-ahead. Or he may have some pretty strong feelings and even discourage you from pursuing his ex. If this is the case, hear him out. If he has objections, try and understand why, and then you can consider your options.

Your friend may never come around to the idea of someone he knows getting involved with his ex. While this might not be ideal, you still have the option of asking her out and seeing what happens knowing you have reached our to your friend first. It is a scary prospect to risk compromising a friendship for a girl, so if this is your situation, try and consider if you would be willing to risk losing your friend over this woman. It's best to understand the stakes of your decision and the possible consequences. Hopefully, you will be able to maintain your friendship and pursue a relationship with this woman.

Good luck,
econfidant

Have a question about your one-true-love or latest fling that you just can't share with your friends? Rachel Begelman and Sarna Lee founded econfidant.com to give you the smart, one-on-one advice you need. You can ask that single pressing question or sign up to ask unlimited questions. Read more about econfidant.

Have a question for econfidant.com? Ask it here...they'll answer one question from a Centerstage reader each week.