Wedding Woes

How do I be okay alone and single?

Dear Prudence,

I am a woman in my 20s, and I find it impossible to stay single. I have been in serious relationships since I was 13, with no real breaks in between. I have spoken to therapists about my codependency and self-esteem issues, and I logically understand that being alone won’t be so bad once I get used to it, but I just can’t seem to figure it out. I just ended my most recent romantic relationship, and this time I really, seriously want to be single, but I’m scared of falling into my old patterns or just being miserable and lonely until I give in to a new relationship. Do you have any tips on how I can break this bad habit and learn to love being a strong, independent lady who doesn’t need a man?

—Struggling with Singleness

Re: How do I be okay alone and single?

  • Therapist is a good start; but making a boundary and sticking to it is important too. If you want to be single- commit to that. Tell (potential) partners when you meet them you’re not interested in that. 

    But also- find some hobbies, fill your time with something besides another person! 
    short+sassyei34
  • All good advice @charlotte989875.  I wonder about this person's status with their friends too.  

    At that age, I had a group of girlfriends where we all ran in a pack, going out and whatnot. We had guys in and out of our lives, but having my little group helped keep my life in balance and I didn't get into relationships that much because I had my friends to occupy my time. 
  • levioosalevioosa Southern California member
    Seventh Anniversary 5000 Comments 500 Love Its 5 Answers
    FSIL B could have written this letter. Except she’s not as self-aware. 

    Therapy, LW. 


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    charlotte989875mrsconn23
  • I haven't been truly single since highschool. I really wanted a break after my ex and I broke up. But DH and I were already friends and I tried sooo hard to NOT date him but he refused, lol. 

    LW definitely needs to continue with therapy. They didn't have any time in life to grow up, figure out who they were without a partner, all their coping skills likely include someone else. 
    charlotte989875short+sassy
  • CharmedPamCharmedPam Chicagoburbs member
    Sixth Anniversary 2500 Comments 500 Love Its First Answer
    I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:

    Casadenamrsconn23charlotte989875levioosa
  • I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:
    I think for some people it is just the way life works out, for others though they CANT be single.
    charlotte989875
  • I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:
    There isn't anything wrong with it, as long as people are doing it from a place of strength.

    People should feel comfortable with their own company.  And not anxious or like they are missing something.  

    When people feel like they HAVE to be in a relationship to be "whole", it can potentially lead to bad outcomes.  Like getting into a relationship with the wrong person, just so they are with someone.  Or cheating on their current partner, so they can immediately jump to a new relationship 
    Wedding Countdown Ticker
  • I've seen people who are incapable of being alone to the point that they've rushed into marriage after the death of a spouse and the next marriage did NOT go well. 
  • levioosalevioosa Southern California member
    Seventh Anniversary 5000 Comments 500 Love Its 5 Answers
    I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:
    There isn't anything wrong with it, as long as people are doing it from a place of strength.

    People should feel comfortable with their own company.  And not anxious or like they are missing something.  

    When people feel like they HAVE to be in a relationship to be "whole", it can potentially lead to bad outcomes.  Like getting into a relationship with the wrong person, just so they are with someone.  Or cheating on their current partner, so they can immediately jump to a new relationship 
    Agreed. I haven’t really been truly single for a significant amount of time since I was out of high school. I was with my ex for almost 7 years, then we broke up and FI had been waiting for me (we were friends and coworkers). I was literally so excited to be single. I had the whole next three years planned out with how I was going to maximize my time without an SO, lol. But then there FI was, and people like him don’t come around very often, so I said fuck it, I’m dating him. And I don’t regret it at all. I do wish sometimes I had a bigger gap in between relationships but I wouldn’t change it at all if it meant losing FI. I’m also super independent, sometimes detrimentally so. I’m probably a little too comfortable being alone. Lol. 


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  • kerbohlkerbohl member
    Ninth Anniversary 500 Love Its 1000 Comments First Answer
    levioosa said:
    I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:
    There isn't anything wrong with it, as long as people are doing it from a place of strength.

    People should feel comfortable with their own company.  And not anxious or like they are missing something.  

    When people feel like they HAVE to be in a relationship to be "whole", it can potentially lead to bad outcomes.  Like getting into a relationship with the wrong person, just so they are with someone.  Or cheating on their current partner, so they can immediately jump to a new relationship 
    Agreed. I haven’t really been truly single for a significant amount of time since I was out of high school. I was with my ex for almost 7 years, then we broke up and FI had been waiting for me (we were friends and coworkers). I was literally so excited to be single. I had the whole next three years planned out with how I was going to maximize my time without an SO, lol. But then there FI was, and people like him don’t come around very often, so I said fuck it, I’m dating him. And I don’t regret it at all. I do wish sometimes I had a bigger gap in between relationships but I wouldn’t change it at all if it meant losing FI. I’m also super independent, sometimes detrimentally so. I’m probably a little too comfortable being alone. Lol. 
    Same!  I don't regret being with hubby, but I did have so many plans before him!

    levioosaCasadena
  • MyNameIsNotMyNameIsNot Atlanta member
    Knottie Warrior 5000 Comments 500 Love Its 5 Answers
    I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:
    There isn't anything wrong with it, as long as people are doing it from a place of strength.

    People should feel comfortable with their own company.  And not anxious or like they are missing something.  

    When people feel like they HAVE to be in a relationship to be "whole", it can potentially lead to bad outcomes.  Like getting into a relationship with the wrong person, just so they are with someone.  Or cheating on their current partner, so they can immediately jump to a new relationship 
    One of my best friends is like that. I love her, but she doesn't always make the most rational choices. She's always been a serial monogamist. When she'd break up with someone, it was never more than a week or two before she had a new boyfriend. Which in itself isn't a problem, but she'd settle for whoever was handy to avoid being single. It meant some really shitty boyfriends, and also did a number on her self esteem, which meant putting up with even shittier boyfriends. It's a hard cycle to break out of.  
    charlotte989875levioosaVarunaTT
  • kvrunskvruns member
    5000 Comments Seventh Anniversary 500 Love Its First Answer
    I have a friend like this.  I’ve never known her as a single woman... is it bad to not be single?  She seemed OK with it..:
    There isn't anything wrong with it, as long as people are doing it from a place of strength.

    People should feel comfortable with their own company.  And not anxious or like they are missing something.  

    When people feel like they HAVE to be in a relationship to be "whole", it can potentially lead to bad outcomes.  Like getting into a relationship with the wrong person, just so they are with someone.  Or cheating on their current partner, so they can immediately jump to a new relationship 
    One of my best friends is like that. I love her, but she doesn't always make the most rational choices. She's always been a serial monogamist. When she'd break up with someone, it was never more than a week or two before she had a new boyfriend. Which in itself isn't a problem, but she'd settle for whoever was handy to avoid being single. It meant some really shitty boyfriends, and also did a number on her self esteem, which meant putting up with even shittier boyfriends. It's a hard cycle to break out of.  
    I worry about that with one of my friends. She and her exH had a trial separation in Jan of 2019, she found out he was seeing someone else (who she had suspected) a couple weeks later and was on a dating app with a new bf by Feb 2019. She now has a baby with new guy, they're married (the one I recently mentioned saying they did a court house ceremony). He is a nice guy from what I can tell, and I really hope it lasts.  But I've known her for 20 years and she has always had a serious relationship and never more than a few weeks between then so I'm always nervous. She was supposed to be single for a while after the separation but clearly that didn't happen. She doesn't know how to be single. 
    mrsconn23short+sassy
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