“Like shopping at Goodwill”: People over 40 get brutally honest about what dating is really like

21.11.2025 13:00

The Daily Dot

Middle-aged singles on Reddit are sharing stories about the horrors and surprising upsides of dating in their 40s. As you might expect, a lot of folks are finding it difficult, especially with the rise of dating apps and an overall decline in mental health.

For a lot of people, no matter what age, dating is a difficult journey. Especially if you're in a rush to partner up, it can be frustrating and even soul-crushing. There's no shortage of responses from people saying they've given up on the endeavor and learned to love the single life.

For those who still want to try, it can help to be prepared for what's out there. Thankfully, one Reddit user asked for stories from those who've already walked the path.

u/cardanolovelace via Reddit

"Single people over 40, what's the dating world really like out there?" asked u/cardanolovelace in a recent post.

Before you despair, it's not all bad. A good number of Redditors feel that dating while over 40 is easier than it was when they were younger and less mature. If you can find someone not weighed down by a ton of relationship baggage, you might find your dates to be more straightforward and honest.

Still, there's no shortage of entertaining horror stories and bitter jokes. Prior marriages can complicate things, especially if the divorce was contentious. It can get even worse if your date is in an open marriage rather than actually single.

Just remember that every experience is different, and those who've had it worst are probably the most inspired to respond to this thread. Good luck out there.

1. Worse for people who don't want kids

"I’ve been single and not looking for a year and a half after a LTR, and this is what worries me the most about the possibility of dating again as a CF person.

How do I meet guys my age who don’t have and don’t want kids?? The odds feel very low." —u/orangepaperlantern

2. Sinking standards

"You swipe for weeks and get no matches. Finally, you get one! It's likely a scammer, catfish, or someone looking for moral support. You'll find out after chatting with them, if they reply. The moral supporters are the worst. They ghost when you finally make a move to get a coffee. Poof. Hope vanquished again."

"Eventually, you lower your standards further and further until you match someone real and go along with it because you're lonely as fuck. The people on this level have issues. Mainly mental health. Lots of baggage too. That's if you're lucky!" —u/random5654

3. It's great, if you're in the right city

"I’m in NYC and it’s a lot of fun. There are tons of single, wonderful women in their thirties and forties who maybe prioritized other things earlier in life or refused to settle for less than a great match or moved on from one that wasn’t working for them."

"Even when something isn’t a romantic spark, I still enjoy checking out a new spot and getting to know someone on a slightly more intimate level who you never would have crossed paths with otherwise." —u/cryptopo

4. It's great, if you have money

"I know a rich widower in his 60’s who is having a great time dating, so I guess it’s ok for rich people." —u/LateralEntry

5. Bare minimums, high restaurant standards

"Female, 40, Los Angeles. The apps are full of boring guys who all have photos of themselves at the Dodgers game. And they're all like 'What is the absolute bare minimum I have to do in order for you to pay attention to my d*ck?'"

"I talked to a male coworker (49) the other day, and from his side, he says all the ladies are like 'What do you do for a living and how much money do you have? If you're not taking me out for a fancy meal, I'm not interested.'"

6. People can be mean

"A few years ago I literally had a woman on an app - that as far as I can tell I'd never interacted with or liked - contact me first, and with a long message."

"It was a big long rant about how, someone like me (then) nearing 40 could possibly exist and would dare to go on a dating app when they're renting (I mentioned I was 'renting again' vaguely in my profile) and they don't even own their own home, berating me for thinking that someone like her would ever date such a person." —u/ledow

7. Learn to enjoy yourself instead

"Honestly I stopped even trying. It was messing with my mental health. I realized that I was so desperate for peoples approval, for someone to validate that I'm worthy that I was changing who I was. I now changed my mindset and make sure to enjoy my single years. Travel, explore, have random adventures."

"There is a freedom in solitude that some people would find scary." —u/cursethesunlight

8. Straight to the point

"It’s 'look I don’t got time for f*cking around and games, we doing this or not?'” —u/Zeniant

9. Relationship trauma everywhere

"My dating pool pretty much consists of divorced women and/or single moms. Their previous relationships have traumatized them so much that they are mostly avoidant and are too afraid to be vulnerable or trust that I'm not going to jeopardize their independence." —u/TVs_Tandberg_G

10. Open relationship traps

"Hi I'm Ray, My wife and I have an open relationship because we're too afraid to get a divorce. BTW I can only see you between 8:00am - 8:15am at the Pancake house on Monday mornings according to our rules." —u/opt_out_unicorn

11. Depends how you look at it

"It’s fun. You can interact with lots of interesting people. I’ve met some really nice women and some real awful human beings.

So you either have a nice time or a good story, it’s a win win. Dinners get expensive, but that’s the cost of participating." —u/mushmu77

12. Pretty chill compared to your 30s

"As my dates approached 40, the urgency to close the deal and start a family got more and more intense. Everyone was on a tight schedule to declare go/no-go.

After that, they suddenly went super chill, already had whatever career/house/family they wanted and just cared about good hangs." —u/captcha_wave

13. More honesty, less BS

"Maybe I'm an exception, but dating has only gotten better as I've gotten older. There's just so much less bulls**t. People are generally more honest with themselves and in turn more honest with each other.

It's a lot easier to get to the end of the date and say, 'This wasn't really a fit was it?' 'No, I don't think so.' 'Good luck on your next date, though!' 'You too! Get home safe!'" —u/sloowhand

14. Change for me

"Garbage. People want you to change everything about yourself to be the one for them, but won't change a thing for you."

"And I mean even little things." —u/Mussels84

15. The men need therapy

"So far, I've only been encountering emotionally unavailable men. The lesson I had to learn is to release them back into the wild quickly. I haven't been able to find any secure men." —u/Sludgecupcake