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Dating in the Milwaukee and Southeastern Wisconsin area has to be one of the most fun places to date, considering the number of choices (especially during the summer!) we have at our disposal.

Examples-The lake, all the festivals, the Kettle Moraine for hiking, Lake Country for boating, the proximity to Chicago and the great theatre district we have at our fingertips. One should never have to come up with a shortage of ideas of things to do for a first, second or third date.

What’s more important of course is how do enjoy the date, how you “click” with the other person and how you feel once the date has ended.

A lot of us give the highest ratings to the “chemistry” we have when we meet someone. While sexual chemistry is important, it’s not the be-all-end-all. I personally feel that the most important things are similar values and views of the world and how we manage our way through it. Some close third and fourth imperatives are kindness and empathy.

Having a great date should consist of the following:

  1. Conversation. A give and take and a back and forth in conversation. One shouldn’t be asking all the questions and the other answering. Take turns. Listen. (It’s an exceptional skill to have)
  2. Comic Relief. As they say, laughter is the best medicine-laughter is the greatest ice breaker there is and can sway a date in the right direction.
  3. Respect. Respect for one’s time, one’s effort that was put into the date. And whoever picks up the tab should be thanked extensively. It can be expensive to date.
  4. Acknowledgment to the other for showing up, being present and planning the date. The 5 Love Languages speak here and time and acts of service are two things that people can offer.
  5. Flirtation. Now, of course, this should only be working if you have chemistry for each other. But a bit of fun and flirtation is imperative for starting a connection.

Remember that the give and take are imperative. All of us have been out on dates where we wondered if the other person is remotely interested in us. Even if you don’t click with everyone-which you won’t, it’s important to at least try. After all, that person may know of the perfect person to introduce you to!

Lori Mendelsohn

Lori Mendelsohn is a professional matchmaker. With a knack for introducing people who wind up saying, “I do,” she can be reached at Her website is