Tag: older women dating younger men

  • Are you trying to date men who think they are hotter than they are?

    He’s got a comb over, beer belly, and has donned a wrinkled shirt. Yet he thinks he’s James Bond. George Clooney. God’s gift to women. Why?

  • Dipping into salsa

    Salsa — a spicy dip and a spicy dance. My latest experience is with the latter. Dr. Philling myself, I asked how online dating was working for me. I’ve met some interesting men and gathered a few sweethearts from the experience, but know there are other options. Yet, being situationally introverted, I’m not great about […]

  • I want to date his family

    It’s a bit awkward when someone you’re newly getting to know invites you to a casual family event and you end up hitting it off with his family much more than you do with him! This happened to me this weekend. My new activity partner (AP) and I had agreed to see a movie. He […]

  • Two-step for one

    Yee-haw! Country Western dancing. Let’s go! This was my feeling as I decided to try something new, a bit out of my comfort zone, in my quest to experiment with meeting available men in the “natural” way. Common advice from dating experts is to take a class in something that interests you. So I thought […]

  • “I don’t know if my equipment still works!”

    While munching sushi and margaritas, the sweet, 62-year-old widower shared his concern as we discussed dating. His wife of 3 decades had died 18 months ago and he was dipping into the dating pool. What he found was a lot of aggressive, sexually hungry women. He was dumfounded that they tried to seduce him on […]

  • Casual sex

    His online profile mentioned that he loved sex, something that is usually a yellow flag as it says the man doesn’t have much of an appropriateness filter. But other things he shared made me give him some slack. Half an hour into our first phone call, he said he “loved, loved, loved sex.” He suggested […]

  • Authenticity vs. strategic phoniness

    I was listening to my friend Mike Robbins speak to a group about his newest book on authenticity, Be Yourself. Everyone Else is Already Taken: Transform Your Life with the Power of Authenticity. He’d asked the audience a few questions about what value authenticity has in our lives and then he asked why being authentic […]

  • Is he selling too hard?

    “You’ll never meet another guy like me” he said confidently during our first phone call. I refrained from saying “Duh. Everyone’s unique,” but I decided it would be better to play along. I wanted to see what he thought was unique. “How so?” I asked, curious about what he’d say.

  • Royal wedding — good or bad for midlife daters?

    I’ve just returned from the royal wedding. Well, not the wedding itself, as my invitation must have gotten lost in the post. However, I let it be known to my British friends that I was available for anyone’s plus one. I would have dashed out and bought a fascinator! I was in London for a […]

  • Love advice from a Frenchman

    A few days ago, over a pain au chocolat in Paris, my French friend Benoit shared relationship advice. While it was something I’d heard before, somehow coming from a Frenchman in Paris, delivered in his charming French accent, it had more gravitas.

  • The benefits of flirting

    I like to flirt. I don’t ever expect anything from it. I’m surprised if there is a benefit beyond just fun. This week I had an experience that cemented my belief in harmless flirting. Not that I needed any encouragement!