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In Portland, by contrast, most of his friends were in long-term relationships with people they’d met in college, and were contemplating marriage.

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.

Past girlfriends had complained about his lifestyle, which emphasized watching sports and going to concerts and bars.

He’d been called lazy, aimless, and irresponsible with money.

Before long, his new relationship fell into that familiar pattern.

“I’ve never been able to make a girl feel like she was the most important thing in my life,” he says.

“It’s always ‘I wish I was as important as the basketball game or the concert.’ ” An only child, Jacob tended to make plans by negotiation: if his girlfriend would watch the game with him, he’d go hiking with her.

He was passive in their arguments, hoping to avoid confrontation.

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.

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