I Haven’t Dated In Over Twenty Years So I Asked Women Of All Ages for Advice
Photo Julie Delpy and Ethan Hawke in Before Sunrise (1995)
Story by Rachael Moshman
“Don’t settle with the first person you kind of like. Meet LOTS of people”
I didn’t date in my teens. I was painfully shy and had horrible self-esteem. Then I finally got access to the Internet and made a profile on the now extinct Yahoo! Personals. Starting conversations with people from behind a screen was so much easier. However, I was still convinced no one would like me, so when the third guy I went out with showed interest I didn’t bother to evaluate how I felt about him.
I was 20 when we met and married him at 21. Then suddenly I was 40 and realized I was incredibly unhappy and unfulfilled in my marriage. I didn’t like the example I was setting for my daughters, so I moved into a temporary rental by the beach and filed for divorce.
Learning to live on my own, getting two girls through high school and off to college, and finding some solid footing was a big undertaking. It’s been three years and I’ve only gone on two dates - and one of those was unintentional. I have no idea how to date and am self-conscious about my lack of experience.
So instead of just diving in, I decided to do some research by polling women of different ages about their experiences and asking for advice. Out of curiosity, I even asked a couple of men. I quickly found a common theme: dating pretty much sucks for everyone to some degree.
Dating in the 20s
Annie started dating after high school and quickly realized she was attracted to personality, not gender or sexuality. As a server in a restaurant, she came in contact with a wide variety of people every shift. “It’s a myth that all men want to hook up and all women want to settle down,” she said. “Women can be just as horny, adventurous, naughty, and casual as a stereotypical man - sometimes more so! I dated and hooked up for years without wanting a serious relationship.”
Madelyn is 21 and has already struggled emotionally after putting everything into relationships only to feel neglected, rejected, or that her boundaries were ignored. She now tries to remind herself that “the world has too many people to count, so there’s no point wasting your time being upset over someone who isn’t on the same path as you.” She admits this isn’t always easy to remember, but is working on getting to know and love herself so she doesn’t settle for less than she deserves. I sure wish I had that wisdom at 21!
KacyLolita Carvajal is a musician who has dated people she met at gigs, as well as through dating apps. She’s met some “cool people” and a lot who have made her cringe, especially dudes on dating apps throwing Latina stereotypes at her or calling her “hot tamale” in the first message. She went out with a guy once who then called her to bail him out of jail. She declined.
All three of these young women say dating is all a numbers game. “Don’t settle with the first person you kind of like. Meet LOTS of people,” Annie urged. “Get to know people and let them get to know you. Don’t try to change anyone and don’t change yourself for them.”
On a positive note, KacyLolita and Annie both now have partners they’re very happy with and assure me finding love is worth all the bad dates.
you might also like…
The Male Nude & the Female Gaze
When 46-year-old photographer Jennifer Folsom picked up her camera, something shifted. She no longer felt invisible. In fact, she felt powerful. And she wanted to explore her reclaimed visibility in a way that made sense to her: through art. She shares what she learned about desire, gender roles, and life after embracing the female gaze in this conversation with fellow artist, Melanie Biehle. [read more]
Dating in the middle
Angie is 36 and says scrolling through the apps is depressing. “Men my age look so old and everyone seems like they’re on the hunt for a rebound fling after a toxic relationship.”
Ginny is 40 and got divorced the same week as me three years ago. However, she started dating much faster than me. Hats off to her! She’s had more fun dating younger men than men in their forties, though she is a bit nervous about being labeled a “cougar.”
Both Angie and Ginny have found there’s a wide range of life phases happening when people are in their thirties and forties. Some people are newly divorced or even widowed, while others have never been married. Ginny is forty with a preschooler and has been out with men who have grandchildren around her daughter’s age. Angie has a teenager and doesn’t want a baby (and recently had a hysterectomy), but many men her age are just now wanting to settle down and start a family.
When asked if they had any advice for me, Angie laughed, “Good luck! Dating sucks!” Ginny said, “Make sure your confidence is high because the apps can be soul crushing.”
Ginny advised using an app that best matches up with your interests. “Stir for single parents. Hinge for dating. Tinder for hooking up.”
Katie, who is 40 and has been on 25 dates in the past year, always starts with a coffee date. “It doesn’t require a huge time commitment, but you can usually get a good read on someone.” She says Tinder is “a whole pile of trash and fake accounts.” She recommends OKCupid or Bumble.
However, my friend Brit had a great Tinder experience. She realized she was a lesbian and left her husband just before her 40th birthday. She quickly met someone perfect for her on Tinder and they recently celebrated their first anniversary.
Dating over 50
Ami and Susan are both dating in their 50s after leaving marriages they were in for decades. Ami says the most challenging part is getting to know who someone truly is. “It can take months or even years for someone to really show who they are. By that time, you may have fallen for someone who doesn’t even exist. Then you suddenly realize you’re in a relationship with someone who isn’t real.”
Susan says, “I’ve been using dating sites. It’s like looking for a needle in a haystack. There are so many fakes and weirdos out there. And I don’t mean just odd. I’m talking truly bizarre.” Her advice is to not expect much. “Look at dating as a new hobby or a way to meet potential friends. And even if they check off most of your boxes, if you don’t feel chemistry, don’t settle.”
Jo-Anne is 55 and refuses to use the dating apps. “I have a friend with benefits I’ve known for decades. We can go months without talking. I’m learning to love myself. If I never have another relationship, that’s okay.”
What do men say?
“The consensus from women seems to be that dating sucks,” I explained to a few male friends. “What are your thoughts?”
“Yup, that pretty much sums it up,” Andrew agreed.
Chris said he’s interested in a committed relationship, but finding women who match the “energy” he wants to bring to a relationship is a challenge.
Ryan said being a man who dates other men doesn’t make dating any easier.
If we all agree dating sucks, why does society put such a high priority on it? Maybe because it’s a very profitable industry. According to Business App, dating apps brought in a combined $3.08 billion in 2020. North America contributed the biggest chunk of the pie (mostly from Tinder and Bumble). Millions of new users download dating apps each year. According to Maslow, love and connection are basic human needs. So maybe the hope of happily ever afters like Brit, Annie, and KacyLolita have found shine so bright we forget about all the ghosting, calls from jail, and awkward encounters.
So do I feel any more ready to date after doing all of this research? Stay tuned...
Rachael Moshman is a writer, educator, and thrift diver. She’s on a journey to find herself after marriage, motherhood, and divorce. Follow along at www.ramblingrach.com.