Dating Advice While Doing Overhead Presses, Lunges, Squats and Bicep Curls

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

A lot happens at my gym. What I mean by that is, a workout I plan will take 45 minutes takes an hour and a half because I end up talking to people I know, largely about relationships. So, what ends up happening is, I’m listening to stories and then offering divorce, relationship or dating advice.

Here is a story I thought might be of interest. A few days ago, I spotted my friend “Amy” on an elliptical machine. She has been divorced for a few years. She’s completely adorable and like so many other men and women looking for love, meets all kinds of characters who we end up chatting about while working out.

Amy tells me these crazy stories, most of which are kind of unbelievable. Here is the latest: Amy began dating this guy she met online named Rich. They went out a few times and she thought everything was great. One day, out of the blue, Rich texts her to tell her that he can’t see her anymore. Things are just moving too fast and he needs to focus on his kids and career. End of Rich. Amy is sad, but moves on.

She then meets this guy Joe, who is a widow. They go on a few dates and it is going quite well. So, a few days ago, guess who texts? Rich. He wants to get together again. She asked me, “Should I give him another chance?”

Here is what I told her (while we were doing overhead presses, squats, lunges and bicep curls.)

I have nothing against Rich. For whatever reason, he felt the need to push back. He didn’t do anything that upset Amy (other than disappoint her by ending a relationship she found extremely promising, and actually, that’s no small thing. Plus, he ended it via text, which is cowardly and rude.) But, he was upfront with her, he didn’t lie, and he didn’t exhibit any behavior that warrants Amy to never speak to him again. So, should she go out with Rich again?


What she was really asking was, “Does he deserve a second chance?”

I told her that she absolutely should give Rich a second chance, BUT (and this is a big but) be cautious. Rich has already shown her who he is. I remember an old saying, “If someone shows you who they are, see it. They shouldn’t have to show you again.”

I personally think everyone deserves a second chance, but not a third. So, maybe Rich just freaked out. Maybe on the date, he is going to tell Amy how sorry he is, how much he messed up, what it was he had to deal with and why he felt the need to end it with her. That’s what I’d like to believe, anyhow. But my gut says that if he let Amy go, he will do it again. I hope I’m wrong.

I’m a huge believer in the philosophy of the book “He’s just not that into you.” If a guy really wants you, he will make it happen.

Joe, on the other hand has a clean slate. I love the guy because up to this point, he’s done nothing to jeopardize the relationship with Amy.

When I was in my twenties, I put up with so much bad behavior from the men I dated. I let them treat me badly at times, I put up with cheating, and I think because I was so young and insecure, I lacked the confidence to say, “I deserve better than this.”

I can honestly say, approaching my 50th year of life, I have a zero tolerance policy for bad dating behavior. I think it’s because I am so totally fine with being alone if the relationship is anything less than perfect. (Not that I’m saying there is such a thing as a perfect relationship. There are always going to be issues.) But perfect meaning that I am treated the way I feel I deserve to be treated.

As we were stretching, I told Amy the same thing. Go out with Rich again and hear what he has to say, but don’t be fooled by his charm and the sentimentality of how much you really liked him. And, don’t settle for anything less than YOUR perfect.

As for Joe, don’t let going out with Rich cloud your judgment, or you could end up ruining a relationship that got off to a really, really good start!

Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

4 Responses to “Dating Advice While Doing Overhead Presses, Lunges, Squats and Bicep Curls”

  1. Jess

    The job/kids stuff is boy-code for:

    “I met another girl I’m more into than you but I wanna make sure you’ll take me back if it doesn’t turn out… Then I can use you for sex while I look for another girl better than you.”

  2. Chad Stone


    Your friend Amy definitely needs to take your dating advice, which is always wonderful. But tell her about a great new book called The Love Magnet Rules, too!

  3. Steve Friedlander

    I had a close, but not quite the same situation. I was dating a lady that I really cared for, but one day she said her ex-boyfriend wanted another chance. They dated over five years and she felt she had a lot invested not to try it again. Here’s the rub: he was a drunk, gambling and physically abusive. Of course he promised to change…again!
    three weeks later she called me saying it didn’t work out and wanted to see me again. I said no because I felt her thought process of going back to an abusive relationship just because she invested five years with him. If was really difficult as I really liked her. I’ve questioned myself several times, but as much as it hurt felt I did the right thing.
    Your thoughts?

    • Jackie Pilossoph

      I think you should give her another chance. maybe one more date? five years is a long time, and even the healthiest of people get emotionally attached and make bad decisions.


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