I talk to a lot of Chicago men who have their lives together (good career, good friends, good apartment, etc...) and are somehow still stuck single like they were three years ago.
It's rarely a confidence problem. What I hear on the ground is:
"I keep meeting the same women in the same places..."
Chicago is a big city with small-town social mechanics. There's the Wicker Park crowd, and the Lincoln Park crowd, and the finance crowd.
These are genuinely warm communities, but if you're trying to find a woman who hasn't already dated all of your friends, it can be hard to break out of your social milieu.
"Summer flies by, and I don't want to wait another year to find my person..."
Sometimes it feels like Chicago's social calendar is compressed into five months. Memorial Day through
October, the city is incredible
Then the weather gets cold, and the invites to parties slow to a trickle. If you didn't hop into a relationship during the good months, it can be hard to build momentum, and you're waiting until spring.
Matchmaking removes the seasonal dating pressure entirely. My team hustles year-round, and we find women who are serious regardless of the temperature outside.
"The apps are a grind, and nothing else seems to work..."
Chicago has a wonderful population of women who want serious relationships, but the apps fail to filter for that. You can end up messaging women who are keeping their options open indefinitely, going on dead-end first dates, and starting over and over and over.
Basically, Chicago can be a harder city to date in than most single guys will admit. If this resonates, let's chat about how I can help!
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