Relationship Advice: Three Women Who Deserve So Much Better!

relationship advice

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

I have some really great relationship advice. I’ll start off by saying, there’s a lot to be said for getting older. In a way, I hate it, mostly because of medical things that start to happen and the vanity aspect. For example, I recently had my yearly physical and now, all of a sudden, my blood pressure is higher. Add to that that I’m looking in the mirror last week and I thought I had a hair on my forehead, only to realize it was a new wrinkle! Fuck!

But, there are so many wonderful things that happen as you get older: you get smarter, more open-minded, you like yourself more, you stop caring about what other people think, you’re nicer, you’re more patient, you are happier just for little things, you appreciate people more, and you are a better partner in romantic relationships.

My theory is that in general, people’s expectations in romantic relationships and especially after divorce increase with each decade. What I mean by that is, in our twenties, we settle for things we shouldn’t, we put up with bad dating behavior, and we ignore red flags. In our thirties, after being hurt a few times, we put up with less. As we get into our forties and fifties, the real wisdom sets in. My dad used to say, “A wounded dog is a wiser dog” and that really hits home in a lot of older people.


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There is another time when men and women let others treat them poorly: when they get divorced and start dating. That was personally my experience 15 years ago. The first guy I dated after my divorce was a nightmare. He was hot and cold, and at the time, I put up with it because I had such low self-esteem (a byproduct of being newly divorced) and felt like that was how I deserved to be treated.

When I see people being treated badly in relationships, it upsets me because I know that deep down, that self-esteem is there, it’s just temporarily for whatever reason, not available.

I recently received three emails from three different women—all seemingly devastated by the actions of their boyfriends and asking for relationship advice. These emails frustrated me. Why?


Because while I feel for these women, I want to say, “Is this kind of treatment what you think you deserve?!” Have your standards gotten so low that this behavior is something you are willing to tolerate? I want to tell them to take a deep breath, pull their shoulders back, pick their heads up high and move the hell on! In other words, they deserve better! In fact, they deserve only the best!


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Here are excerpts of the emails, followed by my comments and relationship advice.


1. He is still having sex with me even though he has a girlfriend. 

What I want to know is, why are YOU still having sex with HIM?? He has a girlfriend. Is that OK with you? I can’t imagine that you enjoy feeling badly about yourself, which is the only thing that comes from sleeping with a man who has a girlfriend. Oh wait, I forgot low self-esteem, sadness, lack of self-love and lack of self-confidence.

Those things also come from sleeping with a man who has a girlfriend. Don’t you feel like you deserve better? When did it become OK to settle and rationalize that sleeping with a cheater is acceptable? Please have the dignity to stop sleeping with him and realize that there are so many men out there who want to be in a monogamous relationship, and that you deserve to be with one of those men. If your response is, “Well, Jackie, where are they? I can’t meet any normal people,” then I say it’s because your mind is blocked because you are sleeping with someone.


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 2. Last night he tells me he’s leaving me, he doesn’t love me anymore and I’m not moving with him.  I have begged him to let me come with him. I am only asking for 3 months and if by then he still feels the same I’ll leave, but we have nothing to loose by trying, yet he will not budge. * (this woman and her husband have been living apart for a few years due to their jobs. Now, the husband got a new job and he and his wife were supposed to move to the same city—finally.)

Here is my relationship advice. You should not have to “beg” someone to make it work with you. I understand that you are trying to make your marriage work, but it sounds very desperate, like you feel you are lucky if he lets you move with him. The attitude instead should be, HE should feel lucky if you move with him.

Actually, you should both feel lucky to have each other. He obviously doesn’t feel this way and I’m so sorry for you. But, “he won’t budge” means it is time for you to accept that things are over and start to rebuild your faith in yourself. I have no proof of this, but is it possible he could be in another relationship?

If you find out that is the case, I am so sorry, but I won’t be surprised. Someday you will be with a man who you won’t have to beg to keep loving you, because he will be committed. Isn’t that what you deserve??


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3. My boyfriend ended things with me, stating he needed to focus on his son and their relationship and getting him through the separation. His daughter is also apparently not able to deal well with the fact her dad is dating as well. So now, here I am single again.

He of course states that it is not me or our relationship that is a problem, just timing and perhaps lack of thinking about whether his kids or he was truly ready to date. I feel like I have been cut off and left to just feel the heartbreak which I feel.


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I feel your pain and in the past I have had a similar experience. It’s awful. It stinks. It’s unfair. But the bottom line is, he has to deal with his baggage and you are powerless to that. He should not let his kids be dictating if he has a girlfriend or not, but it isn’t my place (or yours) to tell him this.

My gut says he will try to get back together with you and it might or might not work out. He doesn’t sound like a bad person, just a confused recently separated guy trying to find his way. You should focus more on yourself rather than on him and what he is going through.

Go out and meet people. I’m not saying jump into another relationship, but you owe him nothing. Go out with your girlfriends and flirt and talk to interesting people and do fun things. You have already gone through the pain of a divorce and you deserve to be with someone who won’t doubt the relationship, someone who is firm in his conviction to be with you and who will not let you go or lose you.


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Did you notice that in all of these scenarios there is one recurrent theme in my relationship advice?

It is: “You deserve better.” As I said above, I think that older, divorced women are so much more willing to accept and settle for situations that they know deep down aren’t right for them–just like we did in our twenties.

I am not judging because I have done it in the past. It’s easy to rationalize and talk yourself into relationships that in your heart you know aren’t right, and to tolerate bad behavior because you don’t want to be alone again or you are afraid you will never find anyone as good.

But I personally think (and this is based on my own experience), the happier life is one that is finding joy in every day, whether you are with someone or not. The better life is being without a man versus being with the wrong man.


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The best relationship advice I can give is to: do things you love to do, surround yourself with people you enjoy being around, who you know truly care about you, and do things that make you like yourself-like acts of kindness, giving back, being a good mom, making good decisions.

These things promote self-love and confidence and independence and empowerment. And that is exactly when Mr. Right will walk into your life.  The bottom line—ask yourself, “Do I deserve better?” If you love and care about yourself (which you should) then the answer is a no-brainer yes. You actually deserve only the best!

Like this article? Check out “9 Signs of a Healthy Romantic Relationship”

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    3 Responses to “Relationship Advice: Three Women Who Deserve So Much Better!”

    1. Dor

      Good advice to the three women.
      The have low self esteem and will settle for the wrong men.
      I don’t think when you are in your twenties , you are noticing the red flags.
      That’s when you are so young and want to marry and believe in the fairytale happily ever after.
      When you older , maybe ififties and divorced, then you see the red flags clearly.
      The fairy tale doesn’t exist.
      You don’t have to be married to be happy.
      Enjoy dating.
      Don’t settle for the wrong man.
      Have fun, go out, enjoy your friends.
      Spend time with your adult kids
      Be happy with yourself.

    2. Caroline Byrne

      Loved this. Letter 1 resonated with me. 3 years and thought better to have something than nothing at all. I know. Very low self esteem. I’m still not better and may never be but I keep trying


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