I grew up the only child of older parents (who are also 10 years apart), and often felt like an awkward old lady trapped inside a teeny-bopper’s body. I admit, I wasn’t as physically attracted to him as I had been to other partners. Have you ever seen a girl with a hideous boyfriend and thought, “Seriously, how the f$*k did he pull that off? Either he's just a nice friggin’ dude; or being with him boosts her self-confidence. The Olsen twins both have boyfriends 20 years their senior. I got that; but even though I knew there was no future, I didn’t cut it off completely. A 50-year-old playing 30 grew past its prime for me. If Mary Kate or Ashley was approachable and not icy fashion prodigies, I would love to ask how they make it work. After it ended, he talked to a lot of people about our relationship -- and what happened through the grapevine was unexpected. Women judged me as having an ulterior, economic motive: “She just dated him for his money,” or “She thought she could get ahead.” In our society people are so quick to judge a young, naïve woman -- never the older man who perhaps should’ve known better too. I have a friend who’s been married to someone for more than a decade who is 20 years older than her. I wasn’t sure how it would go, yet there he was, charming the pants off them all by himself, busting out his A-material small talk with some friends in a corner. Instead I shoved a cracker in my mouth and mulled over her question as I pretended it was hard to chew. Yes, my new man was older than me, much older than me. After politely playing 20 questions with Sue about my new boyfriend, I knew this was the one she was getting at.My new tall, dark and handsome boyfriend was standing across the room looking so fine in his shirt; I couldn’t take my eyes off him. Meanwhile, I was at the snack table and before I could curse myself for leaving him to go in for another cheesy cracker, I was accosted by a buddy’s wife I barely knew, a bitch named Sue. I wanted to say something like, “He’s not as old as those frown lines make you look,” or “He has the biggest d**k I’ve ever seen!
He revelled in the praise his friends piled on him for enjoying the perfect lifestyle — a stunning house and, of course, the icing on the cake, a nubile young wife. I watched with morbid fascination as my husband — sporting a pair of comfortable loose-fitting trousers, calf-length brown socks and his favourite Velcro-strapped sandals — strutted about our terrace like a bantam cockerel.Time creates wisdom – but it also creates responsibilities and complications – mortgage, kids, career, etc.All of this makes dating more and more complex as we get older. Still, most of them fail miserably, for the exact same reasons that I think Penelope is suggesting.In my case, the age gap was actually a cavernous black hole defying space and time. Another lesson in dating: a fling with someone in your professional/personal circle is more often than not bad news. He’s old and sick now, and she takes care of him (even financially), but she’s still partying and sleeping around. I sometimes imagine what would have happened if I had stayed with my older man. The last I heard, my older ex was in a tumultuous relationship with another 20-something, this time a singer reminiscent of Björk. There’s a dating adage out there that you should judge a man by how he treats his mother. Maybe you’re freshly single after a long relationship. Maybe, like I once was, you’re just tired of people asking you if you’ve... Karen Finn Major breakups, like divorce or the end of an engagement, knock you down in just about every way imaginable. Read more Hi there, I don’t know your story, or what has led you to choose dating online.We hadn’t had sex for over a decade, and it was highly unlikely we’d ever make love again.At 67, my husband had been seriously ill for the last ten years of our marriage.But let’s not pretend that we, as a culture, don’t worship at the altar of youth. He’s got the job and the home and the car, and been divorced with a kid already.If you’re over the age of 40 and have ever said, “But I’m told I look five years younger than my age”, then you’re not immune to it yourself. And nobody has more choices than a 28-year-old woman. So if a woman finds it more appealing to just step into that world – to jump from the prolonged adolescence of the late 20’s into full-fledged settled-down womanhood – that could make sense.