Whenever the topic of “settling” comes up on this sub so many people shout “Never settle! I met the love of my life at 30 or 40-whatever and I’m so glad I waited!” That’s great for them, but hindsight is 20/20. Of course you’re glad you waited because now you have someone great.

For the people who are still single because they took this advice, what’s your perspective? As you continued to date and not find that great person, is there someone you wish you had “settled” for?

25 comments
  1. There’s relationships I wish had worked out more favorably(example: they hadn’t moved for work), but there’s no one I wasn’t enthusiastic about that I wish I’d settled for.

  2. No, I don’t have anyone I wish I had settled for. Usually, after I quit talking to someone for awhile I realize what was or wasn’t reciprocated. I might die single, but at least I’ll be fairly happy and low drama.

  3. I wish I settled for my ex. He has a lot of money but he’s a shit person! Doctor with a god complexity that can never be wrong. He purposely talks bad about people and didn’t care how anyone felt after. He told me to just shut up and take what he gives me and don’t talk about my feelings because he doesn’t care. True jerk but in hindsight I should’ve sucked it up. I would be a housewife living on a few acres of land, taking care of my dogs, cleaning and playing video games all day. I might still have a chance but it’s hard to deal with someone who’s so mean. He’s 40 and still single for a obvious reason!

  4. Just here to check on honesty of the comments. This one should be interesting in a few hours.

    I think that putting settle in quotes will turn some people off as this seems to put it in the negative sense but There have to be some people here that can look back and honestly see that “yeah, I should have married that guy or girl”. Especially after the dating sorrows I see here on a daily basis.

    Let’s see how honest we are today.

  5. None at all. Maybe only ONE person I should have at least gone out on a second date with. And I’ve been single 6 years now and slim pickings out there for me….

  6. Yes. M who I met when I was 25 was kind and she was smart in a kind of soft way. I wanted someone with more sharpness and wit, that’s what I respected. I wasn’t mature enough to recognise what a Grade A partner she was in every regard. She met someone who she got married to when I was around 31.

    I did actually meet my unicorn at 32 but she was nine years younger and I didn’t let it click and take her seriously romantically until it was too late and she was with someone else.

    Then there was the source of all my problems who was smart and funny but completely emotionally closed off due to prior trauma…but I should have been far more direct.

    So many mistakes. Now I’m 42, I have untreatable mental illness caused by antidepressants, that I have to manage while still holding down a job. I’d still quite like to have a child or two but time is against me and my options are virtually none. When you’re in your 20s you never realise you’re on a timer. I keep thinking to myself…if I only had one more real chance, but will I ever get it?

  7. Yes… she was such a sweetheart, smart, beautiful, fit, and was really really into me. I started seeing her right after a bad breakup, so that muddied my feelings and kept me closed off. She was also a total starfish in bed, and I just couldn’t get over that at the time. She pops up in my mind from time to time, and sometimes I wish I hadn’t broken it off… but it wasn’t meant to be and thinking otherwise is just melodramatic.

  8. I don’t know that I settled at the start, but staying in a relationship I wasn’t happy with brought me years of depression, misery, and therapy. Do not recommend.

  9. Absolutely not.

    I once was in a LTR with someone really sweet and stable. I stayed with him for two years after the moment I realized I had lost feelings for him. Partly because I thought that it was just a phase and it would pass (at least initially), partly because I felt so incredibly safe with him.

    With time, it became increasingly hard to bear being with someone who I no longer loved and who I didn’t even want to kiss. Every little thing he said and did started to annoy me. He, of course, noticed that I was distant and more irritable and I believe he felt very sad and anxious about it. I became miserable and found myself crying inconsolably at a café while talking about it with a close friend and I knew I had to let go even though I was terrified to leave him (I’m am expat, we had just moved to a new city and he was the only one I knew there). Long story short, I learned my lesson. Settling can make both parties utterly miserable and it’s not fair for anyone. My ex is now in a happy relationship (I believe) and he would have been able to find someone who truly loves him earlier if I had let him go and not wasted his time.

  10. No regrets necessarily, but there’s a few I wonder about. That’s life though. There are literally endless choices we make that could have brought us to so many different places. If I had stayed with him, where would I be today? I could be happy, I could be sad, who knows.

  11. Nope. Never. I was told by one girl she was sorry she didn’t settle for me back in the day though. Felt pretty disgusting.

  12. Yes. It was my first real adult relationship and lasted quite a while. However, I let little annoyances (that seemed big at the time) take over my thoughts and thus began a destructive thought pattern of thinking I could do better.

    At the time, I thought that if I stayed, I was “settling.” Now that I’ve had a lot of additional dating experience under my belt, I can reflect back and realize what I experienced wouldn’t have been “settling” at all. In fact, it will probably be the best relationship I will ever have. I just wasn’t in the correct headspace to realize it.

    The moral of my story is: be careful what you think is “settling.” The grass is not always greener.

  13. Not me.

    Generally I don’t think the advice of “don’t settle” is always good, some people need to settle on some things, other people need to not settle so easily. I think it’s important to realize which kind of person you are and settle on the unimportant things, while absolutely not settling on the important things, and to be sure the things you think are important are really important and not just “nice to haves”.

  14. all of my past relationships were with people I settled for, my requirements were that they were interested in me. I’ve always been so lonely that anyone showing interest was good enough for me, regardless of the red flags. all of them ended horribly, so because of this I will never settle again.

  15. One of the best parts about being nonmonogamous is how it allows you to sidestep the whole “settling” debate entirely. I never have to evaluate anyone based on their potential of being my “everything person”, and instead I can let the connections I make develop organically into whatever makes sense for us and our needs.

  16. Not really. There were several guys I had 1-2 dates with that I could have given it one more date with but anyone I had more than a handful of dates with I am still certain of my decision

  17. Yea. Two actually, one still in play. I was never in love with them but they are both close friends that I do love. They’re both kind caring men who have always treated me well. They’re both total catches that I just happened to not feel romantically inclined towards. I’m happy for the married one and like his spouse, I think he’s happier with her than he would have been with me and I love seeing him happy with his beautiful family.
    The one still in play is my best friend and while he makes sense in a lot of ways if we didn’t work out I would lose my best friend. He’s dating someone now who I like a lot, hoping they work out because he’ll always know he wasn’t the first choice and it would bother him, even if he’s thought he’d be alright with it.

    I don’t want another shot with or feel I should have tried harder with any of my past relationships

  18. I’ve often imagined what life might be like if I had settled when we didn’t have matching lifestyles. in all scenarios, I can only imagine misery settling for a life I didn’t want!

    there are some loves that I wish had worked out. guys that I would have been amazing with, but they wanted kids. or guys that really made me feel seen, but we had some major essential incompatibility that we couldn’t get over. I don’t regret that I didn’t settle, but do sometimes pine for what could have been had everything been different…

    thinking back on these doesn’t make me feel sad or nostalgic or anything. it helps me realize that I was truly loved and desired, and that these things couldn’t have worked out. it makes me appreciate what I have and how I’ve grown… and solidifies the standards that I’ve built. so I do appreciate the question coming up every once in a while 🙂

    when I think about the people who didn’t settle for me, I can understand my pain and anger at the time but at the end of the day I’m glad they didn’t. in most of those cases, I can see where it probably wouldn’t have worked out anyway.

  19. Yes, I think so. She was a really sweet woman and cared a-lot for me. The time since that relationship hasn’t exactly been great. I can certainly imagine a happier version of myself with her than the one I am right now. I will say those feelings change though. The moment someone comes along that takes my eye, I’m excited and interested in that new person and would very much like to see where this new ‘opportunity’ might go. When single and alone though, I definitely wonder if I made a grave mistake to my overall happiness.

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