Ask Lisa! Am I A Jerk For Dating Two Women At Once?

July 5, 2009



Dear Lisa,

I’ve been looking for dates and possible girlfriends online for quite some time. I met one weeks ago, and we’ve been chatting ever since. Last night she gave me a card and told me she was thinking of me, although she also mentioned we’re friends first and foremost. I agree and look forward to meet her someday, but also went back to the personals and replied to another ad. I got a message today from someone that suggested we meet today, which we did. We had a good time and even ended the whole thing with a hug and a smooch.

Even though I haven’t committed to any of them yet, I feel like I’m starting to date two girls at the same time, and I don’t think it’s fair to any of them. I had to tell the one I met today about the woman I’ve been chatting with for the sake of honesty (and I hope I don’t regret it.) But on the other hand, I might have to say to one of them we can only be friends, and I don’t want to hurt anyone either.


Dear Two-Timer,

First of all, hats off to you for being such a sweet, sensitive guy and not wanting to hurt anyone’s feelings. There are too few people like you in the world. That said, there’s nothing wrong with pursuing two women casually. The key is to keep things honest, and don’t enter into an exclusive relationship if you want to keep playing the field. You have two choices here, as I see it. You can take a wait-and-see approach with both women, and fess up if one or the other asks about any other ladies who might be lurking around in your life. Or, you can decide which of these two girls you like the most, drop the other one, and pursue an exclusive relationship with the girl you like. Either way, you have to do what’s comfortable for you. It sounds to me like you’re a one-woman-at-a-time kind of guy (there are women all over America cheering right now) and you’ll be most comfortable picking one girl and seeing it out.



Is He Cheating by Lisa DailySome guys ARE jerks for dating two woman at once. They’re called cheaters. Is your guy one of them? Find out here: Is He Cheating?


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