She's Almost Perfect

Q: I think I might be in love. I'm a 36-year-old that works in the city. My friends and family refer to me as a ladies man because I'm usually with a different girl each week. I won't lie, it's been fun, but two weeks ago while I was at happy hour at a bar near my office, I began talking with this new woman. She was pretty, but there was something else about her. To this day I can't seem to figure it out. She's not like any girl I've ever been with, and I find her very interesting. We talk all the time and have gone on two dates since our meeting. I feel like I really connect with this girl, and she may not just be a fling like all the others, but there's one thing holding me back - her age. She's 54. -Brian, 36

Dr. Anna: This is a tough one for you. Better to start with asking yourself why her age such a concern for you? Are you worried about being judged by friends and family? Are you worried she will not want the same things you want? Are you wanting marriage and kids and worried that she isn't? If you are in a rush to settle down, probably better to talk to her about that in the beginning. But if you're not in a rush, why not give yourself permission to enjoy the present moment and let yourself have this different experience.

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