A
male
 ,
anonymous
writes:My female peers are, on average, older than me (although they often think I’m older). I’ve dated older women in the past but they always seemed to be three steps ahead of me and it puts a horrible strain on the relationship. At the time, I had just started my university studies and hardly had a career to envision myself as a dependable provider anytime soon. They were steadfast, looking for kids and marriage and firmly pondering “When?”. So I freaked out and like a fool I learned my lesson, twice. It was all too serious, too fast.I’ve dated younger women in other social circles but I keep gravitating towards the women with whom I study. Granted my personal situation has changed, but my past spurs worry about the headache and heartache dating an older woman might once again bring. They will always be ahead of me career-wise. I’m very interested in, and keep thinking about, three stellar women in my class.* The first (close to MY AGE), I’m ATTRACTED to and my personality and interests are COMPATIBLE with hers. Relative to the others, she is LIKELY to reciprocate my interest.* The second (an OLDER woman), I’m VERY ATTRACTED to and my personality and interests are COMPATIBLE with hers. Relative to the others, she is VERY LIKELY to reciprocate my interest.* The third (an OLDER woman), I’m VERY ATTRACTED to and my personality and interests are VERY COMPATIBLE with hers. Relative to the others, she is UNLIKELY-somewhat likely to reciprocate my interest. (Although I haven’t really tried yet! :-)An outside opinion on my thoughts would be great! Which one would you pursue? Do you have any general advice on dating older women? Should I maybe keep looking in other, younger social circles?
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reader, anonymous, writes (19 January 2009): I think you should date all of them! It never hurts to ask and you have nothing to lose. I was wondering about your quote: "Granted my personal situation has changed, but my past spurs worry about the headache and heartache dating an older woman might once again bring. They will always be ahead of me career-wise." Does that bother you? You sound like a very smart man and very able to hold your own when you do finally settle on a career. Just make sure the one you love is equal in that aspect too. I don't want you to be a puppy dog to some older woman just because she doesn't understand you or can't connect with you on that level. Definitely date them all. Good luck to you.
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