Women reveal what really happened when they dated men who’ve always been single: 'The results here are either marriage or them turning out to be complete weirdos, no in between'

Author image for Isabella Penn
Isabella Penn
Jun 22, 2025 7:00 PM EDT

In the world of dating apps where you can meet someone, analyze their Spotify anthem, and decide their fate all within 30 seconds, apps like Hinge claims to be "designed to be deleted." Cute in theory, until you realize the algorithm seems to think you're only compatible with men who list "5'11" (but 6'0 in shoes)" and have a suspicious number of fish photos.

Eventually, you may opt for the old-school approach: meeting someone in real life. Maybe it's at a friend's party or a painfully long wedding weekend, and you actually vibe. But what would you do if he casually drops that he's never had a girlfriend? Like, ever. Is that a green flag or a glaring red one? Depends on the guy. Maybe he's been focused on his career, healing from trauma, or just hasn't met the right person. Or maybe he's emotionally stunted and thinks lifting weights counts as a personality trait.

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  • Turns out, there’s no middle ground here. As women in this thread reveal, dating a guy who's always been single ends in one of two ways: marriage… or a therapy bill.

  • "Women who gave the guy who's been single his whole life a chance, how did it turn out?"

    Cheezburger Image 10519433984
    via Molly the Cat For Unsplash+

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • Zestyclose_Visit4834 I dated a 28 year old guy who never even kissed another person until me, never went on a date etc. It didn't work out but it didn't end bad either, it ended very amicably. I think
    via Zestyclose_Visit4834
  • he was very used to and happy being alone that being that intimate with someone else may have been overwhelming for him at times, otherwise the lack of experience didn't really affect things significantly.
    via Zestyclose_Visit4834
  • He is one of the most genuine and nicest people I know though and we are still good friends today
    via Zestyclose_Visit4834
  • christine-bitg Not me, but friends of mine. They met at a party i hosted. I was friends with both of them separately before the met.
    via christine-bitg
  • She was divorced or getting divorced amicably from her first ex. He had been single his whole life. They were both in their 40s at the time. They celebrated their 25th anniversary last month.
    via christine-bitg
  • Cheezburger Image 10519434240
    via Patrick Nguyen For Unsplash+
  • Acc3ssViolation Love how the results here are either marriage or therm turning out to be complete: weirdos, no in betweens
    via Acc3ssViolation
  • Piksu4444 He thought nobody could love him. When we were together, he said we are two people that nobody could love. I didn't want to share his misery, it ended very quickly.
    via Piksu4444
  • glamasaurus Well, not his whole life but I got into a relationship with a guy who said he was single for 10 years. What I didn't know is that he had never been single. He just didn't count those women as actual girlfriends. So not great.
    via glamasaurus
  • DBones90 I'm a guy, but my partner has a dis lity that puts her in a wheelchair. As a result, she hadn't been in a single serious relationship before we met. She even had a big blowout for her 30th birthday because she figured she was never getting married.
    via DBones90
  • A month later, we had our first date, and we celebrated our fifth marriage anniversary just the other day.
    via DBones90
  • ThrowRAIka Figured out even before we got together that he's been. single because he's awkward, unsure of himself and has never really put himself out there. But he's honestly one of
    via ThrowRAIka
  • the sweetest guys I've ever met. He's a good listener and is pretty in tune with his own feelings. I just feel really comfortable and happy in this 6 months we've been together.
    via ThrowRAIka
  • Of course, there're still some obstacles. He's still kinda awkward at times about being a boyfriend. And while he's aware of his and other's feelings, I still kinda have to pry sometimes for him to open up to certain things.
    via ThrowRAIka
  • Old-Importance 18 I'm the single guy. I've alway been very insecure around women.
    via Old-Importance18
  • I've had few, and short-lived, relationships throughout my life until I met her in my late thirties, a gorgeous woman who, I don't know what she saw in me. She says that, like Jessica Rabbit, I make her laugh.
    via Old-Importance18
  • We've been together for eight years now and are married. She makes me feel like the happiest man on earth.
    via Old-Importance18
  • SnarkSnout My friend married a pilot in his 40s, never married. Met at church. After marriage, h wouldn't have s with her (she was thin and gorgeous by anyone's standards). She
    via SnarkSnout
  • pressed for reasons, wanted to start marriage counseling. He finally said the reason he wouldn't have s was because she "wasn't close enough in her relationship to Jesus". Turns out he was a repressed homosexual. He never admitted it and was nasty hateful in the divorce.
    via SnarkSnout
  • morbidemadame In private he was a sweetheart. Then we met his group of friends (all single men in their 30's) and he tried to belittle me and position himself above me in front of them, kinda to show them he was some sort of alpha male since he now had "a girl".
    via morbidemadame
  • At first I thought it was insecurities or something; let's say I excused him. I tried to talk to him about it; it didn't change a thing. So I've put him back in his place and walked out, and I made sure to do it in front of his friends since apparently, they were included in our dynamic.
    via morbidemadame
  • Keyspam 102 He's my husband and we've got 2 kids
    via Keyspam102
  • shutupphil He had a very weird idea of what women want and refused to listen what I want, did not respect boundarie It ended badly.
    via shutupphil
  • AmyGranite I was his first girlfriend at 20 Married by 28, divorced at 41. Hopefully his new boyfriend appreciates my efforts of raising him up.
    via AmyGranite
  • Ghost Of YourLibido Bad, there was a reason he was single his whole life. Clingy, controlling, possessive, but also once he got a gf thought he was hot sh and started trying to cheat and failing. Terrible.
    via GhostYourLibido
  • suckstoyerassmar He'd had one long term girlfriend ten years ago ir college, but nobody had warranted a second date since then. He was just selective and picky. No clue
    via suckstoyerassmar
  • why he saw me and went "that one right there, that nutcase is for me." We're very happily married!
    via suckstoyerassmar
  • Flat_Refrigerator151 Lovely, best partner I've ever had.
    via Flat_Refrigerator151
  • CrazyBroccoliPT So from comments they're either the best person ever or really really problematic
    via CrazyBroccoliPT

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