Chicago has no published Group weekend. Group coaching there is available on request, and a Private Bootcamp takes three consecutive days that you settle with us once you have booked. Pick the days with the winter and the lake in mind: Chicago winters are generally cold and snowy, and Lake Michigan shapes the weather in every season. If you typed chicago cold approach into a search box, you want a coach with you in the field while you approach women, and that is what the three days are.

Choosing days for a Private Bootcamp

After you book, everything is arranged by email. You coordinate the city and the dates with us, and your coach then calls you for a short introduction before day one and agrees the exact times.

Sessions are scheduled around work. Weekday training begins in the evening, and a weekend session starts in the afternoon.

The weather is the main thing to think about. Winters are generally cold and snowy, and the city is a little windier than the average American one. Summers are hot and humid. Whichever season you choose, the lake has a say in it. Plans change. Tell us early enough and the Bootcamp can be moved once, to a future date.

What the three days contain

The days are daygame and nightgame. Daygame happens on the street and in cafes. Nightgame happens in bars and lounges. Every approach gets coaching as it happens, and every set gets feedback after it.

Expect two four-hour sessions a day, 24 hours of coaching spread over the three days. How the time splits between daygame and nightgame depends on what you most need to practice, and the coach adjusts it to you.

Private means you and the coach alone throughout. Group, where it is arranged on request, never seats more than three students with a coach.

A written practice plan, short and specific to you, comes at the end. Your coach also adds you to the private community Slack, and you hold on to it afterward.

What a dating coach says about Chicago

a dating coach picks Chicago as a city that is big enough to attract ambitious people and has plenty going on. It is also small enough, and Midwestern enough, that you can talk to women without turning it into a full-time job.

He says going out there has more of a bar feel than a club feel, and that the friendly attitude helps, because it is easy to talk to a stranger there. That is one coach's opinion of the city after time spent there, and nothing more.

A grid that makes the city easy on foot

Here is Chicago as it looks to any visitor. These places are not the Bootcamp's itinerary, and the exact schedule is worked out with you after booking.

Chicago is very walkable because of its street grid. Madison Street divides north from south, and State Street divides east from west. Once you know those two lines, you can place yourself almost anywhere.

The lakefront and the shopping streets

The Magnificent Mile is the stretch of Michigan Avenue from the Chicago River to Oak Street. It is the main commercial corridor between the Loop and the Gold Coast, with broad, busy sidewalks.

The Chicago Riverwalk runs along the south bank of the river, with restaurants, bars, cafes and small parks. The Lakefront Trail follows the western shore of Lake Michigan and is used for walking, jogging and cycling. Millennium Park is a public park in the Loop, and Lincoln Park is a large park beside the lake on the North Side.

Where people go out at night

River North is one of Chicago's top nightlife neighborhoods, especially around Hubbard Street, and it sits next to the Magnificent Mile. Wicker Park is known for its nightlife and food scene and its boutique shops. The West Loop is a former warehouse district whose buildings hold lofts, restaurants, bars and galleries, with popular restaurants along Randolph Street.

Wrigleyville, on the North Side, is one of the city's largest entertainment districts, with many bars and restaurants on North Clark Street. The Loop is the central business district and also holds the Downtown Theatre District.

Getting around on the L

The Chicago Transit Authority runs the city's buses and its trains. The trains are the rapid transit system everyone calls the L. Between the grid and the L, a visitor can cover most of what is above without a car.