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I have a lot of doubt about myself. I'm sure this is true of everyone, to a certain degree, but most of my doubt about myself is in the context of finding love again. I was married for . I got married at 21 and was divorced by 24. Since then, finding love again has proven completely futile. I recently have had my eye on a cute girl at a breakfast diner I go to on weekends.  Her name is Kelsey. I can't show a picture of her on this site, but for your own mental image, picture a 10/10 working at a diner. 
Every attempt at establishing a connection with a woman over the last ended in complete failure. I blame myself, even though I know not to. Relationships are a team effort, and while I know that I can only give my 50%, I still take it pretty hard when love fails to materialize. And failure after failure after dismal failure shakes confidence in oneself, and for a long while I was convinced that I was simply unattractive. Not a healthy mindset to get in. 
My plan is to eventually give Kelsey my phone number. I know it's not cool to ask out a girl while she's working. It's not fair to her, she's being paid to be polite, and asking her out puts her in an awkward position, so I won't do that. Instead, I'll ask her what she's up to for the rest of the weekend, in a small-talk way, and when she says "nothing" I'll respond: "Aww, no big night out with the boyfriend?" Now hopefully she'l respond with "I don't have a boyfriend" because then I can at least pass her my number, which I've written out already on a piece of paper and then just leave. I risk not getting a call back and losing my favourite place to eat on weekends, but I think that's a small price to pay for the satisfaction of knowing that I at least tried my best. And that's the point, right? Trying? I can't for the life of me shake the feeling that it's all futile, and that I'll never find love again. My jaded outlook and overall cynicism prevent me from even feeling slightly optimistic, but I know that mindset can change if success comes my way. To give up, though, that's so much worse. So I'm going to try. I know my chances of success are slim. I know that it is unlikely she's single, and I know that there is a distinct possibility that I'm broken on some fundamental level, but god fucking dammit, I'm going to try. 
This Saturday, I'm going to try.