: 16, 2026 1:05 am : [Hot] Dating an older man stories 2026
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Article:
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. Featured Video.
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. Advertisement. “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. Advertisement. 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. Advertisement. 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. Advertisement. 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. Advertisement. 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. Advertisement. 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. Advertisement. 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. Advertisement. 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. Advertisement. 15. The men need therapy. “So far
I’ve only been encountering emotionally unavailable men.
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