Dating the older woman - what were you thinking?

By Trevor Davis


A friend of mine told me that he was seeing "an older woman" in a very conspiratorial kind of way at the weekend. His eyes lit up like a schoolboy telling a dirty joke when he mentioned it. He feigned not wanting to tell me at first, resisting when I pushed him for details of his Friday night, when he'd hurriedly called to say he wouldn't be making the pub that night, and had hung up without explanation. But naturally I had some questions for him on this rather unexpected turn of events (he's not as suave or sophisticated as Dustin Hoffman in The Graduate), and he eventually capitulated. Are you looking for an older love?! or even a younger one.. try UK Net Guide's Online Dating!

Question One - How old is older? He was 26, and she was past 40 apparently, so I think this definitely qualifies as an age gap. In fact, that's more of a generation gap - where the real concept of the older woman lies. I think its not so much about age, and more about the different stage of life you're at. There must surely be a gulf in life experiences between someone in their mid-twenties and someone well on their way to middle age.

Question Two - How on earth did you meet her? Now I don't particularly have a thing for older ladies, and my past relationships have all been with women of a similar age to mine. But to be honest, this seems largely due to the fact that this is the female age group that I have most contact with - I don't think I've ever really spoken to a 40-year-old woman in a social situation, except my mum of course, and that's strictly a different thing, no matter what Freud says. So how on earth did my friend meet his current squeeze? "Friend of a friend" he says, mysteriously. I press him further and it turned out it was the MUM of a friend.

Question Three - What do you talk about? The problem with a generation gap is that there's generally an interest gap as well. If you're in your twenties and you have the same hobbies as a middle-aged woman, then you've got issues. So where's the common ground? My friend (who I am purposefully not going to name, by the way), came up with a great answer. Essentially, he said, there's often not a lot in common between men and women even when they are the same age. And besides, the whole point of a relationship is to experience new things, and get to do learn about other people's interests outside of your own. So she learns about football and Channel 4 comedy, and he learn about gardening.

Question Four - Any good-looking daughters for me? No answer to this one, and I can understand why. If my friend married this woman, and I married her beautiful 20-year-old daughter, then he'd be my stepfather-in-law, or something like that. And that's just weird.