Do I want to date again after 35 years?

I've been struggling with this question for months, my divorce now officially 15 months behind me. Dating in 2024 is worlds away from 1988. I'm trying to crack the code.

Do men still give women flowers on a date? Or is it a red flag if they do? Photo by Alex Padurariu on Unsplash .

My female friend and I head to the tiki bar while the rest of the meetup singles group frolics in the pool or chats at small tables, dripping water from their swimsuits. My friend and I are wearing sundresses. Donning a bathing suit for my first foray into late midlife dating was decidedly not happening.

My friend, who had been to this group’s monthly single gatherings before, assured me that that the pool was probably only part of the “pool party theme”, that there would surely be dancing to live music in an air-conditioned room of the hotel on this sweltering Florida evening.

But no such luck. Already four hours into the event, the singles in the pool held aloft fruity drinks, chatting away. No one was dancing to the tunes performed by the one-man band near the tiki bar. I ended up talking to a woman, Susan, who sat at our table, a dance studio instructor in black slacks and glittery top, clearly also expecting a cooler room to strut her stuff. By the time I’d heard her life story (“I’ve been single since 1994; don’t get your hopes up”), I telegraphed a look to my friend (“Let’s get out of here.”) She nodded and went up to the bar to pay her bill.

Susan elbowed me. “Hey, look at that guy. He’s watching her. I bet you he’s going to make a move.” A man with thick, wavy graying hair, maybe in his late 60s or early 70s, wearing eyeglasses, a button-down shirt and khaki shorts, was clearly not here for the pool. We watched as he shifted his chair in her direction and then, as my friend turned from the bar, stood up to talk to her. They chatted. I heard my vivacious partner in crime laugh (she’s not slowing down even in her early 70s). She came back to the table. “I’m ready to go. But I have his phone number. He offered to buy me a drink but I said we were going. Keep ‘em wanting more, right?”

Ah, the games people play. I was right back to my 20s, to my teens even, and I didn’t know if I had it in me to do this again. It had taken me 15 months since my divorce was final (22 months since I’d moved out of my marital home) to reach this point, of actually going to a singles event. And already I had no desire to do it again.

I’d set up a Bumble account a week or so earlier, coached by my oldest daughter on how to use it, getting advice from girlfriends on which photos to choose and how to sum myself up in less than 300 characters. Then I flicked through the men’s profiles, the men of a suitable age. “These men are all strangers,” I thought. Which I know is a ridiculous thought because of course they’re all strangers.

Once upon a lifetime ago, my ex-husband was a stranger, too. But he was a stranger who one of my oldest and dearest friends fixed me up with. I longed for that old-school world of dating. The fixup. The best friend who knows exactly the right guy for you. Someone you trust arranging a blind date. Not a first date you’ve set up with a stranger on the Internet, one that comes buried in warnings: meet in public, make it just a coffee; let a friend know where you’ll be so she can check on you later; don’t let him walk you to your car so he can get your license plate number and stalk you. And whatever you do, don’t give him your phone number; only communicate on the app. It all reeked of so much danger. Stranger danger.

To a woman who had last dated in 1988, this was indeed a strange new world. I didn’t know if my lack of enthusiasm for it had to do with lack of courage or self-confidence “to get out there” or not being emotionally ready or—and this possibility kept poking its way through, the way the truth won’t let go of you:

Maybe I’m okay being on my own for now. Maybe I let destiny take its course?

Getting ready to date, at 64

While that thought floated around, others competed for attention. Like, “You’re not getting any younger. The older you get, the harder it’s going to be,” and “You’re lonely, admit it. Wouldn’t it be nice with a male companion? One where you felt an attraction? Your bed has been empty a long time.” Or “Do you really want to be alone the rest of your life? He isn’t just going to walk into your life. You have to go out and find him.” It was like a group of well-meaning aunties had taken up residence in my head, warning me away from spinsterhood.

But terms like that—spinsterhood—are from another era. Surely, we’d moved beyond a woman needing to define herself by being part of a romantic partnership. I began to ask myself: What would emancipated dating look like, dating for grownup women?

Because I do think I want to date. I don’t know that, like Elizabeth Gilbert, I can swear off romantic relationships for the rest of my life and only be satisfied with my female friendships, even though I incredibly value these women. I am too much of a romantic for that. Although there is appeal in how Liz described this truth for her to Glennon Doyle on We Can Do Hard Things in 2022 (influenced by, as Liz acknowledged, her love addiction) :

“I’m just going to have a great life and I’m going to get love, affection, and intimacy through my friends and through my relationship with my higher power and through my intimacy with myself.”

This was something I wanted to figure out about myself. Anyone who knows me well will tell you I am a perpetual student, particularly, in recent years, a student of myself. Starting in 2021, I’d gone down a path of getting to know myself better through a series of courses, programs and books aimed at deeper self-knowledge. One result of all that self-inquiry: I can no longer so easily pull my own bullshit on myself. So when my coach and friend

Nicole Terrell

who writes the newsletter

Fully Expressed

announced a program designed to help women get back into dating after divorce, I jumped at the chance to do some exploration.

Over a period of months starting in late January, Nicole and I talked about the phases of dating, “deal breakers and dream makers” in terms of the ideal partner, beefing up your confidence, where to meet potential suitors, setting up your dating app profile and finally, preparing to get out there. I filled in worksheets and we had our always encouraging coaching calls. Nicole inspires me with her coaching about discovering the innate power of a woman’s own pleasure, as a graduate of Mama Gena’s School of Womanly Arts. I wanted some of that pleasure. In January I wrote in a worksheet that by not dating I feared “I was taking a break from fully living…that I desired the prospect of a romantic partner, to be held and touched and cherished by a man. I feel like I’ve been hiding myself away.”

Six months later, I’m not so sure. Am I hiding or am I liking what I see in the mirror and don’t need that self-regard propped up by a man? Have I retreated from the world or am I liking my new apartment and my family and my friends and my writing and my work and and my frequent travel and my life as it is right now? I am a modern woman who can attend to her own pleasure, thank you very much.

Just recently I saw my friend

Cindy DiTiberio

at

The Mother Lode

parsing this same question. She recommended the great article, On celibacy, solo sex and quitting dating because, "why bother" from

Rebecca Woolf

at

the braid

.

Cindy writes: “Perhaps the reticence divorced women have to dating is they don’t want to give up the authority they have regained as single women. They don’t want to relinquish control. As I’ve talked to other divorced women, we connect about the glory of living alone. The chance to starfish in your own bed, with no one else to make room for. The ability to make yourself nachos for dinner if you want, no man to cook for. We have spent decades of our lives living for others. We don’t want to do it anymore. Yes, maybe we might like some romance some day. But over and over in The Divorce Diaries, I’ve seen women who want to date, but don’t ever want to cohabitate. I totally agree.”

Maybe the answer, for me, is somewhere between the starfish and the octopus who wants to wrap her many limbs around another warm body. I am biding my time while I develop the confidence in myself to avoid becoming once again a codependent partner in a relationship, as I was in my marriage. It’s still true, as I wrote in my worksheet, that “I’m nervous and unsure” about the prospect of dating after more than three decades. But that’s okay. I know my self-worth. For Nicole, I had no problem coming up with 30 reasons why I’m an amazing catch. So I know I’ll get there. It just might not happen at a monthly singles meetup gathering. Or on the Bumble app.

The best plan of action feels like going out and living my great, big, beautiful, expansive life with my arms wide open. And just maybe someone really special will walk into them.

---

FURTHER READING

Here are some articles, podcasts and writers I follow on the topic of midlife dating:

The podcast “Hotter Than Ever” with

Erin Keating

including How To Attract Epic Love with dating coach Lilli Bewley; “Listener Mail: How Do I Start Dating Again After 60?” and (not that I see this as particularly relevant for this reticent dater): Advice: How Do I Juggle Dating Several Guys at the Same Time? Erin is so out there with her bravado and her sexuality and her confidence and it’s truly inspiring. She also writes the Substack

Hotter Than Ever

.

From

lyz

at

Men Yell at Me

, her article, The enshittification of dating apps, where she tells us, “app burnout is the symptom, not the disease.”

From

Kimberly Harrington

who writes

HONEY STAY SUPER

, check out these honest, funny articles about her first forays into dating and sex after divorce: ✨55✨ (Part 1) and ✨55✨ (Part 2) "How is menopause showing up in your dating life?" and You think you want to date a 10, but who you need to watch out for is a 3.

Midlife Dating Tips From expert Amy Nobile from

Shannon Watts

at

Playing with Fire

For some heartfelt smart advice with a dose of humor, check out the latest newsletter from

Sari Botton

creator of

Oldster Magazine

: Ask The East Village Yenta, an advice column for the lovelorn (and others) of any age.

THIS WEEK’S SONG: Thanks again to

Marielle Velander

for the recommendation:

"I am, and I'm wonderful, and I know there's this supreme power that gives me the ability to be everything if I just allow it to happen'

LET’S CHAT:

Have you been dating post divorce or a breakup? What was your experience? Did you have reticence about dating and if so, why? What’s your dream scenario of how to date in 2024 for midlife (or later) women?