Once a Cheater, Always a Cheater?”

Dear Emily.

Two months ago an intern started working for me and right away I was attracted to her. Let’s call her Angie.. After about a month I had resolved to ask her out when another intern, Angie’s roommate, randomly mentioned Angie’s boyfriend.  I still felt strongly about her but wasn’t sure what to do…

I needed to get it off my chest, so after the internship finished, I asked her out to coffee and I told her I liked her.  She said she had no idea.

Then we went out to drinks the following weekend. And lo and behold, clearly she was interested, because we had a pretty hardcore make-out session.

Now the question is, if she breaks up with her boyfriend over the holidays, and we start dating in a month or so, how much should I worry that she’s “a cheater.” One of my girlfriends thinks this is totally not ok, but I don’t get the vibe that this is who she is in general.

Anyway, should I be concerned, or just go with it?

Thanks again for the show,
Alexander

Dear Alex,

No one is innocent in this situation. She cheated on her boyfriend and you pursued a woman in a relationship. You didn’t ask her out for drinks just so you could get it off your chest. You wanted her to reciprocate your feelings and leave her boyfriend for you. People often deny their true intentions to avoid disappointment or moral responsibility.

Now that you’ve gotten what you wanted, do you still want to be with Angie?

There will always be the uncertainty of someone cheating on you. This fear is exacerbated if the person has a known history of cheating. For some people cheating is completely unacceptable. But if  you were staunchly opposed to cheating- no exceptions – you probably wouldn’t have pursued a woman in a relationship.

Don’t take the things your friends say too much to heart. You need to decide for yourself whether you want to be with her. Chances are the advice your friends and I give you will have little weight in your decision. People tend to do what they want, even if they aren’t sure if it’s right thing or if it will work out.

I say just go for it! Enjoy the make-out sessions and worry about the rest later. People dwell too much on the what-ifs. Remember, you won’t be able to find out who she actually is in general if you don’t give it a chance.

xxx,

Emily