The Marriage Lesson That I Learned Too Late

Why Success Can Feel So Bitter

After going to college on the East Coast and spending a few years bouncing around, Jacob moved back to his native Oregon, settling in Portland. Almost immediately, he was surprised by the loveandseek desktop difficulty he had meeting women. Having lived in New York and the Boston area, he was accustomed to ready-made social scenes. 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.

The Long Goodbye to Saturn’s Rings

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. Was compatibility something that could be learned? Would permanence simply happen, or would he have to choose it? Around this time, he signed up for two online dating sites: Match, a paid site, because he’d seen the TV ads; and Plenty of Fish, a free site he’d heard about around town.

“It was fairly incredible,” Jacob remembers. “I’m an average-looking guy. All of a sudden I was going out with one or two very pretty, ambitious women a week. 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. His friends were jealous. Was this The One? They dated for a few months, and then she moved in. (Both names have been changed for anonymity.)

Rachel didn’t mind Jacob’s sports addiction, and enjoyed going to concerts with him. But there were other issues. She was from a blue-collar military background; he came from doctors. She placed a high value on things he didn’t think much about: a solid credit score, a 40-hour workweek. Jacob also felt pressure from his parents, who were getting anxious to see him paired off for good. Although a younger girlfriend bought him some time, biologically speaking, it also alienated him from his friends, who could understand the physical attraction but couldn’t really relate to Rachel.

In the past, Jacob had always been the kind of guy who didn’t break up well. His relationships tended to drag on. His desire to be with someone, to not have to go looking again, had always trumped whatever doubts he’d had about the person he was with. But something was different this time. “I feel like I underwent a fairly radical change thanks to online dating,” Jacob says. “I went from being someone who thought of finding someone as this monumental challenge, to being much more relaxed and confident about it. Rachel was young and beautiful, and I’d found her after signing up on a couple dating sites and dating just a few people.” Having met Rachel so easily online, he felt confident that, if he became single again, he could always meet someone else.