27M, and for one reason or another (the pandemic, lockdowns, and losing my job during that time, although thankfully now back to full time employment) I have been single for 5 years and have only had one date since my last relationship 5years ago. I’ve been focussing on working on myself, I play piano, cycle & swim but worry that having been on my own for so long some women might find this a red flag. Am I overthinking or not?

33 comments
  1. A lot has happened to everyone within the past five years, IMO a gap like yours is understandable. If you’re worried about it, just don’t mention it on dates.

  2. Not at all! It’s a red flag if since the age of 18 you have never been single. Basically never going longer than a couple months relationship to relationship.

    Focusing on self development is absolutely fantastic!!!!

  3. Better to just not bring this up. It doesn’t mean anything until you bring lots of attention to it. Then it becomes an insecurity.

  4. Not a turnoff, definitely overthinking it. Life happens, it is what it is. As long as you don’t make it an issue, a woman is going to think anything of it. If the question gets asked about when was your last relationship, say 5 years ago with assertiveness and confidence, and if they probe, casually say with lockdown etc. it wasn’t a priority. Topic completed.

  5. For the record, I’m a dude.

    Been told several times over that inexperience at over 30 is a dealbreaker and that people are done being training wheels by then. They want a partner who knows what they want and don’t want. It’s fully expected that people work on themselves and date at the same time, there are social milestones.

    Of course, some folks won’t mind, but from personal experience, a lot of people do see it as a turn off.

  6. 28m, been single for 3yrs albeit a lot of dates in that time. Usually if lead with “I’ve taken this time to work on myself” it goes over waaaay better than “yeah I’ve been single for three years”

    Frame it like it was intentional lol.

  7. 29F here. I don’t speak for the rest of the female, I don’t personally do casual relationships so this may influence the way I feel about your situation. Being single for an amount of time is not a red flag for me, what would’ve mattered more would be your intention of going back into the dating game. I would have found it attractive with how you have rebounded from life situations thrown at you. Hope my perspective helps!

  8. It depends on why because depending on the reason it could be a green flag or a red flag

  9. Guy here and Nah man to me it’s not tbh. I haven’t been in a relationship since freshman year lol everything else has been nothing but one night stands. I just wish to find me a girl like Hinata and settle down😢

  10. Generally I don’t like to date anyone who’s been single less than 6 months. Someone who has been single but dating for 10 years is more attractive to me than someone who’s constantly been a boyfriend, husband or otherwise with no breaks.

  11. Nope I’d prefer you do this than fuck a different person every week. You’re totally entitled to that but you’re not someone I’d like to be in a relationship with if you were that type of person

  12. Personally it is a turn off for me because I want a man who wants a woman companion. 5 years content without one is not the kind of man I want.

  13. Honestly, it’s really going to depend on who you ask. Some women will probably find it a red flag but others will probably think it’s a good thing. As with anything, there are people with all kinds of varying opinions out there. I know that’s not the most helpful answer, but it’s the truth.

    Personally, I think it can be very good when someone is able to take time off from dating. There are a lot of people who jump from relationship to relationship and can’t stand the thought of being alone with their thoughts.

    My recommendation is to just not even bring it up unless someone asks and then just spin it in a positive light. Good luck!

  14. I (45f) am dating an incredible man 37) whom was single for 5 years after his divorce. And I mean single, as in only went on a couple of awkward dates and hadn’t even so much as kissed a woman in 5 years. I didn’t know this until our first date (I asked him out) and after hearing what he went through with his ex, it wasn’t surprising that he chose to stay single for so long. Everyone has their own story, and if someone is going to judge you for yours? Then it’s best to leave them in your wake. Had I been scared off by the fact that he chose to hide his heart away for so long I would have missed out on the most amazing man and partner I’ve ever met. We’re now building a life together, and there’s no judgement for our past lives, from either of us. Because, as he told me early on, that’s just the road that brought you here. You will find your person, and when you do it will feel unlike anything else you’ve ever experienced. Just be strong in believing your own worth, and don’t ever settle for less.

  15. Not at your age. A man my age (50) yes I would assume he’s “set in his ways” inflexible and not open to relationships.

    At your age I would assume you were busy building your life.

  16. For me it’s more of a “turn on” depending on how it’s worded. If he’s all woe is me about it I don’t like it, but I really like a guy who enjoys his own time and pours into his passions rather than focusing solely on relationships and having a partner

  17. I’ve been single for long time. Had 1 hooker experience and a few massage parlour trips.. but dating life socks =\

  18. Dude you’re 27. Just say you’ve been working on yourself, just enjoying life, but have been wanting more lately.

  19. No. I prefer someone who has been single a while because to me it shows that they are okay without a relationship and probably worked on themselves. There’s nothing worse than getting to know a guy and hearing how he very recently split from his girlfriend of several years.

  20. Anyone who sees you being single for 5 years as a dealbreaker or a red flag is an idiot, in my opinion. There’s nothing wrong with taking time to figure yourself out and work on yourself, there’s no timeline on how long that should take. In fact, I prefer someone who takes time to themselves instead of filling a void by getting attention from others, and dating or sleeping around with other people. You’ve mastered being alone and now you’re ready to share your life with someone. I personally see it as a turn on.

  21. not personally no because that would make me a hypocrite. I appreciate that getting into a relationship isn’t a given and it doesn’t just happen for everyone

  22. Over thinking, but they might think you only want bedroom activities, but if you do bring this up, explain the why like detailed working on yourself why.

Leave a Reply
You May Also Like