Meet Jacob, a 30-something 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.”