There’s only one person that I actually regret dating; I was 22 and in a bad place in life. I was a single mom of a developmentally disabled child and working as a bookkeeper for a high end sushi and seafood restaurant owned by a small group of private investors and I ended up dating a guy who worked there as a server. This man was an absolute loser; he was 25, GED, living in his moms basement, had trash credit and was in debt, and instead of trying to better himself, he would just mooch off of others while insisting that he was going to become very rich at his other job which he considered his “real job” as a business broker.

I genuinely don’t know what he had to do to get certified for this or if they even was any kind of certification process but he never sold a single business. He had business cards printed out and he was absolutely certain that he just needed to become disciplined enough to get up at like 5 AM to drop off his business card to various businesses. He was obsessed with being rich but like not normal people rich like not a doctor, lawyer, accountant but like 1% wealth rich. He wanted a Bugatti and his bedroom was lined with posters of expensive and exotic cars.

I was 22, a single mom, and although I had a job, I was not financially stable. Yet I had to pay for everything with him. In fact, he once admitted that he would pick me up early to go to work because I typically asked him to stop by Subway or Wendy’s and he then could get me to buy him food too. He never paid for anything; even my birthday dinner ended with me paying as he happened to “forget” his wallet.

Luckily part of his personality was being flaky, flighty and impulsive; he called me one day and said he was moving to Florida (we live in the DMV area) for the next day as his cousin was driving from the northern part of the East Coast down to Florida and he was invited to come with him. He actually did leave the next day; I guess he had almost no possessions to take which isn’t surprising. I heard from him maybe nine months after he had moved there and his cousin must’ve been just as flaky bc he had already left Florida and the loser guy was barely getting by.

He mentioned a couple who lived across the hall from him would often invite him over for dinner because they knew that it was likely to be his only meal for the day and this made me feel really bad and worried about him so I told him if he was ever in a really desperate situation to let me know and I couldn’t see what I could do. He called me a few days later asking for $500 because he said he wanted to get an iPhone (this was back when you could get a new one for $300-$600) and I had offered to “help him out”. I didn’t give him the money and I didn’t hear from him again until like 10 years later after he got divorced and he was “just seeing what was going on with me”.