Can I date my friend’s ex?

I have a few pairs of tickets to give away for Friday's Love Letters screening of "Casablanca." If you want them, e-mail me your casting choices for a remake of "Casablanca" with present-day actors (blasphemy, I know). Keep your entries at 150 words or less. If you've never seen the movie, make some good guesses and include the fact that you're a "Casablanca" virgin in your e-mail. Entries should be sent to meregoldstein at gmail dot com. Write "Tickets!" in the subject line. They're due tomorrow at 9 a.m. I'll notify winners by 5 p.m. tomorrow. If you want to just buy tickets, you can get them here.

I wonder if Alice (as in commenter Alice) will return just to make a point about this letter. For the record, it's not about her. Still ....

One of my best friends is an avid LL reader, and when she heard my dilemma she suggested I write in. I'm hoping you and your readers can help me sort out this situation.

"Jim" has been my friend since I remember -- we grew up together and were always close. After high school we went to separate colleges but continued to stay in touch and get together during every break. His freshman year, he met "Alice" and they began date -- staying together for all four years of college. Since they dated for so long, I hung out with her many times throughout their relationship, going on trips, going out on group dates, etc. Jim broke up with Alice at the end of this past summer after meeting somebody else, whom he began dating almost immediately after ending things with Alice. Because of the time I've spent with Alice over the past four years, I have come to consider her one of my good friends. Having just gone through a rough break up myself, I reached out to her after Jim ended things (after asking his permission to keep in touch with her, which he granted.)

The problem is that I've had feelings for Alice ever since we were introduced. My feelings were simply attraction while she was dating my friend, as I was in a relationship for the majority of time as well. But now that we're both single and we've continued to talk, my feelings for her have grown to something more. Recently, we've had a conversation about how we both have feelings for one another. We went on a date that was absolutely amazing and had a nearly perfect first kiss. However, throughout the night, she did voice her concern that she felt guilty and the only reason she doesn't want to commit to dating me 100% is because she was with my friend for so long. I too feel incredibly guilty -- here I am breaking the number one rule, dating my best friend's ex.

Am I a terrible friend? Is it fair to date Alice? How long do I wait to see if the two of us are actually going to work out before I approach Jim about the situation? Or, despite my belief that Alice and I could be a great fit, should I completely back off?

– A Confused Friend, Boston


You're not really asking me whether it's OK to date Alice, ACF. You've already made that decision. It's happening.

As for when you have to tell Jim, well, the answer is right now. Just be straight with him. Tell him you know the rule ("Bros before … amazing, intelligent women"), but that you've always been smitten with Alice. You're hoping that he has really moved on with this new woman and that he'd like to see Alice happy. Most of all, you're hoping that he'd like to see you happy.

My advice is to tell him sooner than later because "I think I dig Alice" sounds a lot better than, "Alice and I have been dating for three months." Be calm and respectful -- and don't ask, just tell. If you're not really asking for permission, don't pretend you are. Just tell him what's happening and that you're hoping he can put up with it.

There are exceptions to every rule and I hope this is one of them. And if it isn't and he can't forgive, well, it sounds like you're just not as close with Jim as you used to be anyway. I'm not downplaying the importance of old friends, but if you were really scared to death of losing him, you'd have avoided Alice from the start. Instead, you developed a close friendship with her -- one that you knew might lead to more. You've made it clear that whether she's a friend or girlfriend, Alice is your priority. It is what it is. Just come clean.

Readers? Does he have to back off and follow the rule? Is it realistic to think that he should? He's obviously young -- does age play into this? Discuss.

– Meredith