Not thinking about it too much vs. feeling resentful

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My therapist thinks that my constant mental fixation on finding a girlfriend might be doing more harm than help and tells me I need to stop putting so much thought into it. I know it isn't healthy to keep thinking about it and it gets me nowhere but at the same time, I feel resentful at how it feels like other guys have the freedom of choice while I can't because I am deemed "unfit". I am almost 30 (2 more years) and so many people younger than me have already married while I don't even date because my shyness and being considered "weird" by the culture I was born has plagued me for years.

Your therapist is definitely right.

I haven't been able to come to peace with how my 20's have been practically empty when it comes to dating. I sometimes worry I'll be considered "strange" or even a serial killer in waiting to any potential partner if they learned about my past.

kraftiekortie is correct, your therapist's advice checks out. The rumination will only compound your resentment while reinforcing any negative appraisals you may have about yourself in general, the idea of dating, and the idea of love itself. This, in turn, could result in you bringing more baggage to any relationship you may find yourself in, potentially worsening your chances of finding lasting love.

If that sounds bleak, it really isn't. Living more for your own happiness and the happiness of those already in your life will 1. get your mind off of your lack of experience in love and 2. likely make you a happier, more carefree person, making you seem more desirable to a prospective partner.

TL;DR, therapist is right, let it go, be happy. Best of luck to you!

And as for seeming strange, same advice. Ruminating on those feelings is unfortunately more likely to make you look strange to others.

For some it's simply impossible to stop thinking about it or distract themselves, unless they have good hobbies and interests they derive great pleasure from and skill-based ones that require active mental participation and focus, study from university that requires significant time and effort, and/or good friends to hang out with frequently.

Haven't you been trying to stop thinking about it daily for the last decade or so? How's that been going for you? Can you recall a single day you did not feel the aching pang of loneliness at least once, from the moment you woke till you went to sleep.

Personally, I haven't been able to recall one in the last 2 years.

Do you think it would be any easier now, especially at the age where the time you were supposed to 'have fun' when it comes to love and dating is over and you're at the age where it's time to find a woman to 'settle down' with?

I think what you're feeling is natural.

Many men and women begin to completely obsess over finding love when they hit about 30.

There are some that did not care at all in their 20s and were completely single and about age 30 was the age they realized they feel that time is running out for them.

On the contrary, I've heard some men and women say once they reached their mid to late 30s and 40s and such, if they had never had a relationship or only a few many years ago they eventually become numb to loneliness.

So, if things get worse for you from now to about 35, hopefully past that point the pain will only begin to fade.

I don't personally believe that the advice 'you'll find love when you stop looking for it' works for everyone.

It usually only applies to people with a stable friendship group of 3-6 people that they see often, because it means they'll be constantly exposing themselves to people and meeting others through mutual friends or family members of your friends, etc.

When you have this sort of social exposure, you can stop making it a mission in life to find love and just wait until the right one comes along.

Otherwise, if you have very few friends, and spend little time with family, and aside from going to work you don't leave the house that much, you will find that the only way to actually meet anyone at all is through a genuine effort.

All I can say is find what works for you and suits your own lifestyle regarding how much effort you should or should not put in.

Also, trying to get on with your life and live the way you want to for yourself and focusing on making yourself happy, and feeling pain and emotional turmoil due to loneliness are not mutually exclusive.

It's not working. So many things remind me of my singlehood and prevent me from living in the moment. Ten years of depression just can't go away so easily.