A Mother’s Day Gift to Single Moms: The Best Ways To Meet Men

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

As a divorce blogger, I am constantly getting emails from readers asking questions and seeking advice about different divorce issues. I have to say, the most popular question I get asked is, “What are the best ways to meet men (or women)?”

So, as my Mother’s Day gift to all of the beautiful, smart, giving, interesting and hardworking single moms I know out there, I’d like to impart my opinions and experiences on the best ways to meet men. And if there are guys who are reading this, consider this your father’s day gift!

The Best Ways to Meet Men:

1. Dating Websites: I have to be honest, I have never joined a dating website, so I can’t speak from personal experience. But, what I can tell you is, I can’t count the number of couples who have met on these sites. Everyone I know! So, it’s got to be a good way to meet people, right? Here’s the catch. You have to be patient and it’s a numbers game. I compare going on Match.com or other sites to shopping at Loehmans. In other words, you have to sift through some crap to get to a real gem. You have to try on 25 sweaters before you get that beautiful Michael Kors sweater that was originally $110, which you found for $19. Get the analogy? I think there are liars, married people who are cheating, and some real slime balls who join these sites. BUT, there are also countless wonderful, normal people who like you, just want to meet someone. Just be careful. And, if I was going to go on a date with someone I met online, I would drive myself and meet in a public place.

2. Professional matchmakers: I recently did a feature story for the Pioneer Press on a Winnetka based matchmaking service called North Shore Match. Suzy and Amy, two lovely women, personally set you up on dates. They don’t use pictures or computers, they meet every single client in person. They don’t have any formula for set ups, they just go with their gut. So, it’s sort of like your friends setting you up!

3. Networking: This is one thing I feel I am an authority on, because I did it! Here are your explicit instructions. If you want to meet someone, ask EVERY SINGLE PERSON you know to fix you up. Your friends’ husbands, people you work with, your hair stylist, boutique owners, people in your community. You will not appear desperate, I promise! Here’s the thing. No one is thinking, “Hmm…I should set so and so up.” So, you have to MAKE them think about it! Just say casually, “By the way, do you know any single men who might be interested in dating?” Don’t say, “I can’t meet anyone to save my life!” Just say, “I’m single and I think I’m ready to date.” If they have that in the back of their mind, next time they see that cute, single dad, they will think of you!!

4. Platonic friends of the opposite sex: Here’s a scenario. Your friend sets you up on a blind date and you walk in and see the guy. You immediately say to yourself, “No way.” First of all, DON’T do that!! Several years ago, (before I was married) I did that. By the end of the night, I was gaga over this guy, because his personality made him VERY attractive. So, keep an open mind! That said, if you really aren’t attracted to the guy, don’t write him off completely. Try to become friends with him. He most likely has divorced friends. Be honest at the end of the night and ask if he’d like to be platonic friends with you. Even if he’s disappointed, there’s something in it for him, because you could set him up with one of your girlfriends. Guy friends offers so many gifts! You get the guy perspective, you might make a really good friend, and he might end up setting you up with your soul mate!

5. Always Look Your Best: This is one my dad told me a long time ago. Whenever you leave the house, make sure to look the best you can. It takes just as long to throw on your old, holey jeans and tennis shoes than it does to put on a cute pair of Hudson’s, sexy sandals and a necklace. The guy of your dreams might be at the grocery store, or at a gas station (I actually met a guy at a gas station once who I went on 4 dates with!). If you look nice, you will exude more self confidence and it might make the difference if he notices you or not. Think about it, would you strike up a conversation with some cute guy if you feel like you look like crap? No way. I’m not saying you have to spend hours getting ready if you are making a Target run, but just look presentable. The odds go up, trust me!

Happy Mother’s Day single moms!! And happy Mother’s Day to ALL moms!!

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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.

    5 Responses to “A Mother’s Day Gift to Single Moms: The Best Ways To Meet Men”

    1. Simon Solomon

      Great advice. I do have a match.com account profile and to date have not found anyone (or I should say no one has found me) To be truthful all I’ve done is post a profile and left it “out there” much like fishing. I’ve cast out my hook and bobber now waiting for a fish to bite. I’ve had a few replies but nothing became of them. Other than that I am always surveying the landscape inbetween working and fishing.

    2. Lisa Barr

      Happy Mother’s Day … Mother’s Week … Mother’s Year — Jackie — love your new blog, so proud of you … What an inspiration you are to your beautiful children … You Go, Woman xoxo Lisa

    3. Liberated Mama

      Hi Jackie,

      My mom was the best networker when my parents split up back when I was in college, I actually fixed her up on her first blind date! She remarried for 13 years and ultimately divorced again. She is happily cohabitating with her boyfriend of 6 years who she got fixed up as a result of her amazing networking skills. Apparently I didn’t inherit the “dating” networking skills but will give it another whirl after reading your article. You’re right, it’s not a desperate cry for help but a friendly reminder asking people to keep their eyes and ears open.

      Thank you for reinforcing our options of getting back out there again!

    4. Graham Jackson

      Indeed dating as a middle aged bloke is just as scary as it is for you girls. Believe me. There are some strange women out there as well! However. The best advice I would give to any woman out there on Internet dating sites is not to site back and wait. But to actively look and send a message etc. A mans reply rate from women is less than 1 in 10. A woman’s is much better. So if you don’t like who is sending you messages. Perhaps try sending some yourselves. Time to get pro-active.


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