Asking Crush Out – E. Jean Advice on Asking Crush Out With Boyfriend


Dear E. Jean: I’m a guy. I recently ran into an old friend (and former colleague), and we made a date for drinks to catch up. I’ve always had a crush on her. Three years ago, I asked her out, but she declined because she had a boyfriend. Last year, we scheduled drinks (as friends), and her boyfriend vetoed it at the last minute. Should I ask if he’s comfortable this time? Or if he’s even in the picture? —Ethically Conflicted

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E.C., My Caballero: There are three acceptable occasions upon which a man may be “conflicted”:

1. When suffering philosophical anguish over whether to tell a woman that she is beautiful…or that she is stunning.

2. When in the throes of moral doubt over whether to give a woman the small emerald earrings…or the large sapphire necklace.

3. When racked with spiritual uncertainty about how exactly to reveal to a woman that you own a 700-acre estate in Connecticut and a castle in Scotland.

Hesitating about her boyfriend is stupid. He’s not her husband. Take her if you can, sir!

This letter is from the Ask E. Jean Archive, 1993-2017. Send questions to E. Jean at E.Jean@AskEJean.com



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