Follow Us

In my meetings with potential candidates and clients as a professional matchmaker in Milwaukee, I often come across people who have literally just signed their divorce documents and feel they are ready to start dating.

While I admire their gumption, I always advise against jumping in right away. You have so many feelings to process. You can’t be present if you are spending time grieving and trying to figure out what happened. You also have to take inventory of what happened-what went right, what went wrong, and what you will do differently next time. It’s easy to blame our former spouse for all that happened, but I can guarantee that each and every one of us had something to do with it.

For me, the blaring challenge was that I needed to figure out was learning to be happy ALONE. You see, I had grown up with a mother who instilled negativity, who had advised me to marry the first man who asked me, and to be codependent and needy. Obviously, these are not key traits that someone looks for in a future mate, and I needed to get my head around not repeating my past mistakes. I needed to do the work, and I surmise that every single newly divorced person needs to do the same.

So, let’s say that you are ready, have done the self-reflection and are ready to date again. Here are some tips for starting out:

  1. Look at dating as an experience. Like any exercise, the more we do it, the better we become.
  2. Do not go into dating thinking that right out of the gate you will meet “the one.” I did a fantastic job of scaring someone off because I started talking about my gut feelings in him-about our future-and how perfect I thought we were together. (And this was on date #3!!!) In a nutshell, he couldn’t run away fast enough, and rightly so.
  3. Keep a mental list of the “must-have’s” you are seeking. Do you want a man or woman who is emotionally available, athletic, has a great sense of humor? Are you dating someone with those attributes? If not, why not? Your time is precious-so don’t waste it on the wrong person unless you are simply going out to not be alone. I’ve heard stories from men that many women are simply out for free food-please don’t be that person-man or woman.
  4. Realize that online dating is rife with people who are duplicitous. The headiness of being found attractive is certainly a draw and ego booster, but it’s behind a screen-not real life. Realize that online dating means that each person may be dating a number of people and that you won’t be exclusive. Yes, things have changed since our 20’s!
  5. People love to speak about their past relationship failures and how they were “wronged.” When this happens, you can do two things. Change the subject or surmise right then and there that this person isn’t ready to date. This shouldn’t be discussed in the first meeting and for many is a huge turn-off. Try your best to avoid this-and redirect the conversation to other topics.

Lori Mendelsohn is a matchmaker in the Milwaukee area. Her business is www.smartfunnysingle and she has over a dozen marriages under her belt with one engagement pending. She uses her intuition and knowledge of the human condition to match singles.