Whatever age you are, meeting guys can be a bit of a challenge. But what if you want more than a quick, anonymous encounter? What if you want to connect with someone? Get to know their name, how they drink their coffee, or which side of the bed they sleep on? According to marketing executive David Hermann, most people are fairly receptive to starting a conversation:. With that knowledge I can talk to just about anybody.

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Chicago has been flying its rainbow flag for long enough to earn a reputation for being a gay destination. These days, it hosts the third largest pride festival in the U. A mile or so north of it is Andersonville , which was historically home to large Swedish and subsequently Middle Eastern populations but began gaining popularity with lesbians and gays back in the s. It has remained one of Chicago's alternative community hubs ever since, and over the years has been home to everything from feminist bookstores to one of the country's oldest gay bathhouses which is no longer open. You'll find hipster eateries and one of the most successful brans of the national gay burger restaurant and drinkery, Hamburger Mary's.