Online Dating is Less Fun than Being Unhappily Married

Her mouth smiles, but her eyes do not.

Meet Jacob, a thirtysomething, single Portlander on the prowl. He describes himself as “average-looking.” Girlfriends have called him “lazy, aimless, and irresponsible with money.” He doesn’t care much about “a solid credit score,” “a 40-hour workweek,” or settling down. Thanks to online dating sites, Jacob pursues dates with “one or two very pretty, ambitious women a week.” He recently ended a two-year relationship with a 22-year-old; he’s currently juggling flings with “a paralegal and a lawyer who work at the same law firm, a naturopath, a pharmacist, and a chef.”

Jacob, as Atlantic writer Dan Slater frames him, is the embodiment of a new dating market where the allure of “online romance is threatening monogamy.” Whenever he meets another woman online, Jacob (not his real name) thinks: “This person could be exclusively for me, but so could the other two people I’m meeting this week.” Why have a real relationship, Slater asks, when there are so many attractive, successful partners waiting online?

If they make you feel inadequate, then leave

And that was the game-changing truth in how I think about dating. I can’t remember how I discovered it—if I had read it online, in an obscure book, or if it magically came to me in a dream, but one day I realized that the majority of my dating woes could be solved with one statement: If a guy is making you feel absolutely insane, you should step away.

Is Being Alone Better than Dating?

As a single woman living on my own, I often feel the need to fill my time. I pack my days with friends, outings, activities — even when those things aren’t really what I want to be doing. Lately, I’m challenging my tendency to overschedule my life by consciously basking in my moments of alone time, whether I’m lying by a lazy river or chopping vegetables while listening to jazz.

A Typical Bad Dating Experience Turns into Marriage?

My relationship with Thomas began with a seemingly innocuous email he sent to my roommate. 

''What's your friend's story?'' he asked her.

She forwarded his email to me, adding, ''What do you want your story to be?''

I wasn't trying to hide my past. I had been married briefly and left the marriage feeling skittish but hopeful that someday I'd find someone who suited me better. I dated but wasn't drawn to anyone enough to go out a second time. When Thomas's email pinged into my inbox, I felt a surge of excitement for the first time in a long time.