Dear Dee,

I like this girl who just broke up with her boyfriend and I used to date a friend of hers. Can I ask her out? Do I have any chance? I read your column regularly and like the way you think. I look forward to your thoughts. Thank you,

Friend Without Benefits

Dear Friend Without Benefits,

You pose an interesting question and one that the answer will greatly depend on your history with this girl, and more importantly with her friend. For simplicity, let’s call the girl you like, Lindsey, and her friend, Beth. Now, if you dated Beth and the relationship ended badly because of your actions, then you are in a very bad starting place. Lindsey and Beth will right now be sharing notes about lousy boyfriends and you are on the wrong side of that list.

If, however, you and Beth only casually dated, or ended on good terms, then Lindsey may be open to seeing you. My suggestion would be for right now to be her friend and keep it light. If she is just getting over her boyfriend, give her some space to let that relationship end or you may just end up being a rebound. Ask her to go get coffee or maybe to attend a basketball or hockey game and develop a good friendship with Lindsey.  You will know as you spend time together when it is right to move to the next level. If and when it does evolve to the next level, try to lightly bring up in conversation how she feels about dating you and if she thinks her friend will mind. She’ll definitely be honest and upfront with you and she’ll appreciate and respect the fact that you care. Make sure she knows your aim is not to cause trouble or hurt anyone, but that you just really like her and would like to make things work. A little respect goes a long way and hopefully with time you’ll become more than friends…with some benefits 🙂 good luck!

– Dee

Disclaimer: This column is for entertainment only. The author is a student, not a licensed therapist, and this column is not intended to take the place of professional advice. The views expressed are the author’s and are not necessarily shared by The Mirror or its staff.

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