Mr. Unavailable #90: "I Had a Fiancee Once"

This is a Mr. Unavailable flashback circa late 2006.

Vital Stats: 40, 5'6"ish. Business owner, boyishly cute, mischievous grin. Aesthetic: He had that whole T-shirt over long sleeved shirt thing going on. Demeanor: He just seemed so damned self-assured.

First Impression: I met him at a Halloween Party in 2006. I was dressed as a random flower child and he went as himself. His friend introduced herself to me first because he was too afraid to approach me on his own, which was kind of cute. I learned all about the previous three years of his career (self-described bigwig in advertising, left to start his own e-commerce business, which he was then transitioning to a brick-and-mortar shop in DUMBO) and his apartment, which, he said, had three fireplaces.

First Date: Dinner on the Lower East Side. He told a funny story about running half of the New York Marathon and then hopping on the subway and going home. He walked me home afterward and there was some noticeable chemistry.

Signs of Hope: He handled first few dates relatively well: calling, planning, making the first move. Early on, he introduced me to some close friends of his who were visiting from England.

Red Flags: He went to a Halloween party dressed as himself. When he introduced me to his friends from England, the woman was extremely chilly toward me and when I asked him about it, he said with an air of self-satisfaction, "They think no one will ever be good enough for me." (Translation: Most likely, he thought no one would ever be good enough for him.)

He was also extremely preoccupied with what people did for a living and their "goals." He talked a lot about what was wrong with his exes and made it clear he dumped them. He also made sure I knew that he had a fiancee once--bought her a ring and everything, he said, even though, at the time of the relationship, it was clear he was otherwise stranded and friendless at a job in Ohio because, as soon as he was offered a job in New York, he left Ohio and the fiancee behind.

After the first few dates, he didn't seem to know how to handle things and was entirely disinterested in sex. When we were headed back to his place after the 7th date, having still not "done it," he put forth this dreamy invitation: "I suppose we're supposed to have sex all night now." He had an apartment that he paid $3,000 a month for and I was scraping by on a pretty meager salary, but, when we would go to dinner, he would tell me how much my part of the bill was.

Turning Point: I was interviewed on TV about a story I wrote for a magazine I was writing for and, even though it didn't seem possible (re: 7th date), he cooled even more. He threw a holiday party and all but ignored me, instead hanging out with "so-and-so who is a head of advertising" and "so-and-so who runs a music studio." He dumped me a few days later saying he was just too busy with his business and not at all sure about how he felt about anything to have a relationship.

Diagnosis: For him: Despite all his talk about people "going after what they wanted," he didn't actually want anyone else to get what they wanted. He used the fact that he was engaged once as proof--to himself--that he was emotionally available, but, deep down, even he probably knew he wasn't.
For me: I was blinded by what I perceived as confidence and security. It was not to be the first time.