A Mother’s Day Wish: I Want My Mom To Date

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

In honor of Mother’s Day, I thought I’d address a reader’s comment. It comes from a caring daughter who is worried about her mom being lonely, and wants to know how she can help her.


My mother is almost 60. She’s been single for 8 years now. I know it’s because she is nervous about dating. I know she’s lonely. It breaks my heart. She keeps very busy, but it isn’t enough. I just want to help her, but I don’t know how. Any advice?


It is unclear from this reader what happened 8 years ago to make her mom single. Did she get divorced from the reader’s dad? Did the dad die? Is the mom divorced from a second husband?


The reason I bring this up is because the issue of dating after divorce can be very different than dating after the death of a spouse. So, I just want to be clear that if I knew a few more specifics, it might be helpful in offering advice.


That said, I will keep my advice general, and offer some suggestions on how to get mom mingling, dating and maybe meeting someone special and falling in love again.


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Everyone has a different time line when it comes to dating after divorce or after the death of a spouse. I know men and women who started dating right away, since they had felt very alone for a long time while still married. I also know men and women who after years—like this reader’s mom, just can’t bring themselves to get back out there and try to meet people.


I can’t stand when people judge others and say things like, “It’s time (to start dating)” or “You’ve been alone for so long, don’t you want to meet someone?” or “The clock is ticking…” or the opposite, “I can’t believe you are dating already. Didn’t take you long.” Deciding to date is a very personal decision and a very delicate subject for many. So, people should butt out!


My advice to this reader is, don’t push and directly tell your mom she should date, instead, maybe couch it with, “Mom, have you ever considered going on Match.com? I could help you with your profile. We could have some fun with it and just see who’s out there.” Or, “Mom, I heard about a great single’s group that meets every other Friday night for drinks.”



Tell your mom that the purpose of dating isn’t to get married again or even to get serious with someone if she doesn’t want that, but rather to make new friends, get to know others around her age, and possibly find a special connection with someone. That doesn’t have to mean love or intimacy or even sex.


I approach it this way because I think getting back out there just with the intention of making new “friends” is kind of like a warm up to dating and looking for a relationship. Once you put yourself out there, even just a little bit, and you see that others are responsive to you, that they care for you, and that they find you interesting, it is like a drug and you crave more of it. It makes you realize your good qualities and how special others find you. It might make someone realize how lonely they were and cause them to want a special connection.


Another thing this daughter can do for her mom is to encourage her to make some physical changes to make her feel better about her physical appearance. That might mean starting to work out again, eating healthy together, a new hairstyle, a mani-pedi, or working with a personal stylist. That might make mom feel really refreshed and more confident.


Another thing I would tell the daughter to do is to sit down and really talk to her mom. Have a heart-to-heart and ask her why she stays single. She might want to recommend therapy to her mom because there might be some guilt or fear issues stopping the mom from moving on to another romantic relationship.


This daughter seems like a really really good person who cares deeply about her mom. While that is a really nice thing, I have some advice for the daughter, too. She needs to realize that she has little or no control over her mother’s life. Of course she can try to help her mom out of the loneliness, but one thing she can’t do is worry about it and feel guilty. It’s very hard and probably frustrating, but the reality is, the mom needs to help herself. The daughter can jumpstart the process, but in the end, it’s up to mom to find happiness.

Happy Mother’s Day to all the wonderful, beautiful moms out there!

Like this blog? Check out my blog post, “Happy Mother’s Day, You Hot Mom, You!”


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    Editor-in-chief: Jackie Pilossoph

    Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. 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.

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