Friendly, friendly, friendly women—mostly Scandinavian decent with pretty blue eyes, blond, red or brunette hair. Summer time is the time to go. Winter time is too damn cold. There are tons of festivals during the summer and any spot along Lake Michigan (which looks more like an ocean to me) is just going to be great. Surprisingly, this city is cool and sophisticated—with chic bars, lounges and hotels. Stay at the Intercontinental or the Phister Hotel. The former is modern and hip, the latter is old school and elegant. Both hotels will be recognized by the ladies in the city. To stay there gives you instead credibility with the Y.
There are three main areas downtown where you can meet and greet. The first is Waters Street. Places like Water Street Brewery, Bar Louie, Trinity, Buffalo Wild Wings, Sullivans, Magilicutties, Brother and Whiskey Bar are where the 18-23 crowd is—IE the college Y—and Y not. They are young, pretty and fresh. But beware—bring you’re A game. There are lot PB’s here looking for the same thing you are, so be bold and be different. The bars here are crowded, hot and the ratios aren’t the greatest, but you will be fine. Don’t forget how to “hit on the help”, which is gorgeous, friendly and just plain awesome.
Old World Third Street is the next place you should hit up. Bootleggers, Buckhead, Buck Bradleys, Sweet, Apartment 720 and Sojo 7 are where you will find the ladies 23-28, who are in my opinion the easiest prey in the city. Not too young that they are confused and stupid, yet not too old to be angry and jaded. Like the proverbial Goldy Locks and the Three Bears, this area is “just right”. Off the beaten path is a club called Decibel—traditional night club, which is lots of fun.
Jefferson Ave and Kilborn is where you will find lounges like Elsas, Mikeys and Taylors with the 28-35 crowd. Taylors is known for their happy hours, where you can hit on the smoking hot young corporate executive who was transferred to Milwaukee from LA, who initially hated the place, but now loves it.
Want to impress your new lady lover and have a great meal—head to Bacchus, where the Bartolotta family keeps the food and the atmosphere charming and elegant. Umami Moto and Carnivore are other places to bring your women where you are sure to get them all worked up for desert, following the amazing entres.