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DATING AFTER FIFTY: Don’t Sweat It

If you’ve been in a relationship for years, your dating freshness label is way past its due date. “Rusty” doesn’t begin to describe it. How to approach the opposite sex? How to ask for a date? How to flirt? What are the rules? Where are the rules?


There’s this eighteen-year-old inside all of us who went dormant while we were married because our lives were a snooze fest, but when you start dating again, this wanton adolescent jumps up and takes over your body. Let’s get this party started!


Men go all awkward and horny, and women get nervous and giddy (truth be told, women get horny too, but like when we were younger, we’re not sure if we’re allowed). So although we head out there with the belief that we’re mature adults who know how to do this life thing, without warning our hormones start raging again (what hormones, right?), we forget how we’re supposed to behave, and our adult children start looking at us like we’ve gone mad.


We arrive at the first date with that idealized collection of their online photos in our head, scanning the room for someone who resembles them. There’s a good joke going around online:


“If you don’t look like your photos when we meet, you’re buying me drinks until you do.”


It usually takes a few seconds for that static, 2-D version of who you thought you were going to meet to mesh with the flesh-and-blood version who walks through the door. Sometimes it’s a pleasant surprise, other times the person is shorter, heavier or much older than you were expecting, and you’re stuck trying to smile brightly and pretend you’re not shocked. Or, God forbid, someone is giving you that disappointed, “Oh, you’re my date” look. Many a first date has already ended mentally before you sit down. And all because you or they aren’t what you appeared to be online.

The first time I went on an actual, official date after my divorce, I started by freaking out about what to wear. We were meeting at a romantic little Italian place for dinner, so I was going for kinda dressed up but casual but not looking like I was trying too hard. Do guys go through this? I bet you don’t. After most of my closet had been emptied onto my bed, I finally found a comfortable dress I thought might hit the right note. Shoes, shoes. No, not heels. No, not flats. I needed sandals, but not any sandals I had.


I dashed downtown and found some slightly dressed-up yet casual yet not-trying-too-hard sandals. I drove down the road and as I got closer to the restaurant, my armpits started dripping and my heart started pounding. I’d had several phone conversations with my date already and many texts, but suddenly I couldn’t imagine what we’d talk about. I was tempted to make a quick U-turn, go back home, and crawl under the covers.


Instead, I called my daughter, who was in her thirties, and told her I was hyperventilating. Know what she said to me? “Mom, chill. It’s going to be fine. It’s just a person, and you’re having dinner and talking. Maybe it’ll turn into something, maybe it won’t. Don’t stress it.” My daughter knows me well, and is way cooler than I am.


By the time I hung up, I was all zenned out and ready for my date. I cruised into the restaurant and as we took each other in, I could tell this wasn’t going to be a meeting of soulmates. Picture an edgy, artisty L.A. dude with a ponytail and a satchel over his shoulder meeting a demure navy blue T-shirt dress and strappy sandals woman who looks like somebody’s mother. Yeah, not a match. But we still had great conversation and an enjoyable dinner. I met a person and we talked. We never saw each other again and it was OK because it turns out he had three Chihuahuas, which is so not my thing. And that’s how these decisions get made. Mismatched clothing styles, three chihuahuas and you’re out.