TIFU came to a head today but is the conclusion of a long list of FUs.

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[LONG BACKSTORY, sorry}

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I have recently been diagnosed with ADHD after a lifetime of showing the symptoms. One of the outward behaviors of ADHD is risk taking, such as gambling addition or sexual behavior.

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I am married but have never been faithful, I basically "fall for" any woman who shows me kindness and will pursue them if I think there's a chance. Ironically, I usually find sex with anybody except my wife to be a hollow exercise which leads me to look for more instead of doing the logical thing and just keeping it in pants.

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This seeking behavior has lead to a life of massage parlors, online hookups, and prostitutes. I'm not proud and my salary is enough to not have my serial philandering affect household finances or draw the attention of my wife.

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During the pandemic, I started using "paid dating" sites where you agree to pay a certain amount to have a date with a woman. I actually found someone early on and had a consistent and satisfying tryst with them for several months (seeing them 1-2 times a month) but as people went back to work the logistics didn't work out and we went our separate ways.

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All of this leads to the current FU

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[Ok long backstory done]

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A while ago I saw someone on these dating sites nearby who was attractive and was good to chat with. We spent some time talking and then life took over and we lost touch. About a year later I ended up moving the city where she lived and reached out to her. She, a single mother, was having some financial issues, so I offered to help a little bit (just a couple of hundred bucks) and we ended up meeting up and having a fun time together.

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After that, it felt like her life started to fall apart, her wheels were stolen (a real issue) so she couldn't work, I helped with that, then the requests started getting more outlandish but, being the sucker I am, I helped as best I could. At some point she moved across the country to stay with her mother and I didn't hear from her for a bit.

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Then she started again with small "needs" and again, like a sucker I helped out. After the new year, she showed back up in my state and claimed to have a job but needed a little help until pay came in. Again, like the horny idiot I am, I helped.

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All of this came to a head about a week ago when she sent me the listing for a rental property she wanted to rent along with "proof" she had the security deposit and just needed the first month's rent.

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Again, like the total fucking rube I am, I sent her some money.

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Guess what kids? The next morning her "friend" who was going to be helping her pay the rent, etc stole both the deposit and first months rent.

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At every point in this, my brain was like "this is fucking sus" but little head overode big head and my misplaced horniness, combined with what I would like to think is a legit concern for her child's welfare, but I kept helping with what I could.

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Supposedly she's in a place now and has a job and hasn't asked for anything in a week or so, but I checked her Facebook page (I've actually had it for a while and what she said to get money usually matched what she was posting about) and this morning she had tagged the friend who supposedly stole all her money and was arrested for it, in a post about how great friends are.

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I send her a text congratulating her on taking so much money from me but to never get in touch again.

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I haven't heard back what her excuse will be.

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The is 100% on my and my own stupidity and self control issues., but I do have to say after being on ADHD meds for a month or so, my risk taking seems to be much less, so hopefully I will be able to exercise a modicum of self control in the future.

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TL;DR - Prone to risk taking behavior that I didn't realize was part of my AHDH, I let my little head do the thinking and allowed myself to be taken for a non-trivial amount of money by believing I was helping a single mother set up a home for her and her son, with nookie for me being the reward.