To cut or not to cut?

First 2 pics are recent. Last pic is from over a decade ago when I last had short hair.

Have been rocking long hair for over a decade and am nervous to change it. I feel like I'm going to immediately regret cutting it short, but it might be time for a change/update. I'm in my 40s, so my hair has gotten a little thinner since the last time I had it short. I'm not sure what I'll look like now. I think that's what I'm mostly nervous about changing it and why I'm here.

Additionally, I used to get complimented on it a fair bit and have been told by many a woman that they wish they had the length, tone, natural highlights, etc. I'm also single and feel like if I do cut it and finally meet someone, she'll be like "you mean I could have had THAT?" (Referring to a long haired pic of me). (I think this worry was seared into my memory from a Seinfeld episode, and also a cousin who married a guy who had long hair before they met and was in love with his look once she found his old pics.)

At the same time, maybe my hair is why I am single?? I am striking out on all of the apps.

Thoughts? Advice? Recommendations? What should I do to the do? Thank you!✨