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“I’ve never been able to make a girl feel like she was the most important thing in my life,” he says.Whatever the flaws in their relationship, he told himself, being with her was better than being single in Portland again. Now in his early 30s, Jacob felt he had no idea how to make a relationship work. Would permanence simply happen, or would he have to choose it? All of a sudden I was going out with one or two very pretty, ambitious women a week. They dated for a few months, and then she moved in.Around this time, he signed up for two online dating sites: Match.com, a paid site, because he’d seen the TV ads; and Plenty of Fish, a free site he’d heard about around town. At first I just thought it was some kind of weird lucky streak.” After six weeks, Jacob met a 22-year-old named Rachel, whose youth and good looks he says reinvigorated him. (Both names have been changed for anonymity.) Rachel didn’t mind Jacob’s sports addiction, and enjoyed going to concerts with him. She was from a blue-collar military background; he came from doctors.Jacob was single for two years and then, at 26, began dating a slightly older woman who soon moved in with him.She seemed independent and low-maintenance, important traits for Jacob.

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