So I'm in my late 30's and prob can count the dates I been in one hand, and never had a real relationship. None the less I'm extremely lucky to have a very fulfilling, active, full life filled with people that love me, and what not, so I try not dwell on it or get me down too much.
Still it does. It's just a feeling of being alone even when surrounded by people, fear of dying alone, of missing out, etc. I generally keep these feelings to myself, because regardless of how close I am to people, it's such a strange thing to bring up. Finally though, I did mention it to a friend (We were having a conversation about jigsaw as a metaphor for life, and how people try to fit pieces (relationships) that don't fit correctly into their puzzle regardless...I mentioned that sometimes I feels like my puzzle was shipped with a missing piece that will never be there) and she was dismissive, offering the expected "Try something different/love yourself first." Good advice I guess but not what I needed to hear. She profusely apologized when I told her how dismissive and hurtful that was, but that kinda cemented why I don't talk to friends about this.
I have debated going to a therapist....but it feels kinda silly to go just to complain about how I can't get a date. I dunno.
I guess just looking into the insight of what therapy would be like/how to go about entering/what should I look for . I'm not looking for a therapist to suddenly help get dates, more I dunno...to feel better about my current situation.
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You don't sound comfortable with the situation and working through why that is, and what it does to your self esteem, and how you can feel good about yourself independent of others, in conjunction with a professional, might help a lot.
I do find "love yourself first" to be particularly garbage and unhelpful advice in general.
That said, not every therapist will necessarily work for you. One thing that was a huge relief to me back when I tried therapy to help with depression was that you can pretty liberally shop for a therapist that feels right for you. They're professionals, and will generally gladly recommend a colleague if you feel that a particular therapist isn't a good fit. I certainly didn't feel comfortable with my first therapist, the poor chemistry between us just made me want to clam up, but after noticing this she took the initiative and asked if I'd like to be referred to a different therapist.
I wouldn't expect good advice from a therapist about how to get a date, dating sort of sucks in general. They will probably at least try to help with the reasons it bothers you so much.
As an aside. I don't know anyone who is single who doesn't wish they were in a relationship sometimes, or someone in a relationship that doesn't miss being single sometimes. Everyone's afraid they're missing out on something all the time at least a little. So I don't think this is anything that unusual.
A therapist would help you sort your thoughts though I'm sure.