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Here's where to be in 20s, 30s and 40s: In Your 20s 1. New York, New York Another fast-paced dating market that favors the young is the city that never sleeps. in most bars and clubs.) According to data from Match.com, singles in New York initiated the most first dates last year of any other city and 52 percent of women did the asking on their most recent first date. While single women do outnumber single men in this political-focused city, you'll have plenty of dating opportunities.