Dating Game of (mid)Life

Dating and relationships are hard in midlife (and beyond), folks.

First, there’s the challenge of meeting people who A) are single, B) are attractive (to you – there are few universally attractive people), C) have baggage that’s manageable and will fit nicely in the overhead compartment (as opposed to baggage that is falling apart and hasn’t been tended to in the past twenty years).

Then, once you meet someone, there are more challenges: Where do you go on a first date? How long should you wait to have sex? When do you introduce him (or her) to your kids? How soon is too soon to respond to a text? When should we become exclusive? Should I break up with him, or ride it out and see if it gets better?

Then, once you’re exclusive for a while, you might start thinking about moving in together or getting married, and that’s when things really get terrifying: dating someone exclusively is one thing; living with them – sharing a home, and finances, and health issues – that’s a whole other ballgame.

Yeah, sure – younger people have these same challenges, but I gotta tell ya, I think it’s harder for those of us who are older. We’ve seen things, yo. We’ve lived things. We know that we’re set in our ways; we know that we aren’t easy to live with. If we’ve done any self-work, we know that we’re pretty damn screwed up (don’t deny it, because it’s true; you don’t make it 50 years without some stuff messing with your head).

We’re afraid that we’ll never meet someone. When we do, we’re afraid he’s going to turn out to be worse than our ex; when he turns out to be fantastic, we’re afraid he’s going to drop dead. No? Just me? Oh, well…

My point is that, while dating is hard at any age, dating in midlife (and beyond) is more difficult. It’s more fraught with anxiety, and the sense of time running out, and the fear that you’ve lost your shot at love because you’re no longer 35, line-free and with perky boobs.

Over the next few weeks, I’ll be posting a series on dating as an older person:

  • How to meet people
  • First date dos and don’ts
  • The three most terrifying letters to a woman in a new relationship: sex
  • From casual dating to exclusive relationship
  • Showstoppers
  • From relationship to life partner

Until then, talk to me: what questions do you have about dating and relationships? What’s your story – how did you meet your partner, and what challenges have you had in making it work?