The Guy You’re Dating: Does the Glass Slipper Fit?…Or, is it Time to Give Him the Boot?



By Jackie Pilossoph, Divorced Girl Smiling Editor-in-Chief

Dating after divorce is a little bit different than dating before marriage. It is the same in regards to the fact that men and women are out there on dating websites, meeting people, getting set up, and going on dates, as they search for "the one." But, putting aside the baggage factor that everyone has after divorce, which is different than young, single, untainted people in the dating world, there is one really BIG difference: Now, you’re not only searching for “the one,” again. As a divorced person, you’re searching for “the right one” this time.

That means that you might be a little more picky, and you might put a little more thought into things than you did as a young, single, person with such little life experience. And I can say, as a divorced person, if you don’t, then you should!

So, how do you know if your guy is Prince Charming, and if the glass slipper he might place on your foot is a perfect fit? Even more importantly, how do you decide if it’s time to give him the boot? Every situation is different, and only YOU know what’s in your heart, but here are some no-brainers when it comes to the decision to love him or boot him.


  1. He’s pressuring you into marriage after 3 months of dating: Boot him!
  2. He tells you he wants to spend the rest of his life with you after a year of dating, and he doesn’t care in what capacity that is, whether it’s marriage, co-habitation or just dating forever. He loves you and he just wants to be with you. He’ll give you all the time you need. Love him!


  1. He talks about his ex wife and uses the “b” word when referring to her: Boot him!
  2. While he may not have the best relationship with his ex, he respects the fact that she is the mother of his children and his main focus is on them, not her. He’s over it and doesn’t like her or hate her. His relationship with his ex is strictly all about the children. Love him!


  1. You spend hours getting ready for your dates, you buy new outfits, get your nails done, get Botox, lose weight, and he doesn’t really compliment you or seem to notice: Boot him!
  2. You show up at his place in your sweats with no makeup. Your hair hasn’t even been brushed and you have zit cream in four spots on your face. He smiles and tells you how pretty you are: Love, love, love him!


  1. His job isn’t going well and you are afraid you are going to have to support him for awhile: Boot him! (not because he’s a bad guy, but because you don’t truly love him or you wouldn’t be afraid.)
  2. His job isn’t going well and you think to yourself, ‘If he lost his job and I had to support him for awhile, I’d be fine with that because we are like family, and I know he would do that for me.’ Love him! (because truly, you do.


  1. When you have to get together with his family, it feels like an obligation, but you do it because you know it pleases him and that’s what a good girlfriend does. Boot him!
  2. You look forward to seeing his family. They feel like YOUR family: Love him!


  1. When he isn’t feeling well, you let him get his rest and you go out with your girlfriends. Boot him! (let him find someone else who truly loves him because clearly, you don’t.)
  2. When he gets the flu, you go over there with chicken soup and Nyquil and Gatorade and you play with his hair. You don’t even care if you catch it. Love him!


  1. You are constantly going out with other couples because it’s more fun and you want to party. Boot him!
  2. Even after months and months of dating, the two of you still look forward to Saturday night dinners by yourselves. You still sit and talk and flirt and your dates still feel like third dates. Love him!


  1. You just can’t get used to sleeping in the same bed with him. He’s a covers hogger and he snores. Boot him!
  2. You’re loving the naked cuddle, even after years. Love him!


  1. You have completely different political views and are constantly arguing about issues. You just don’t get his stance. Boot him!
  2. You have completely different political views and are constantly having interesting debates and discussions. You respect his opinion and he respects yours. Love him!


  1. You feel lucky that he loves you because he’s so gorgeous, professionally successful, and everyone loves him. Boot him!
  2. You feel lucky that you have each other, and you love the person YOU are with him. You love that he makes you a better person, and you love that he thinks the same about you. Love him!


  1. When he gets home from the gym and you haven’t seen him all day, you joke around and tell him he needs a shower, but secretly you mean it. Boot him!
  2. When he gets home from the gym, and you haven’t seen him all day, you want to throw your arms around him and hug him and never let go. Love him!


  1. You’re having a hard time imagining him fitting into your life with your kids and your family and your career. You tell yourself it will just work itself out. Boot him!
  2. You can’t imagine NOT having him in your life. It’s not even a factor that enters your mind. Love him!
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2 Responses to “The Guy You’re Dating: Does the Glass Slipper Fit?…Or, is it Time to Give Him the Boot?”

  1. Jamie Beck

    I read this and had to smile at some of the comments. I’m still married…but I remember having some of those debates in my head back when I was still out there dating! Of course, if I literally complied with each and every one of these edicts now, I might have to ‘boot’ the hubby (which I don’t want to do)! I mean..he does hog the covers and snore! 😉

  2. Cadbury

    “You spend hours getting ready for your dates, you buy new outfits, get your nails done, get Botox, lose weight, and he doesn’t really compliment you or seem to notice: Boot him!”

    Boot him? Sorry, but I would have already booted her. I know that she’s trying to impress me, but I wouldn’t want to be around someone who has to spend hours getting ready for a date, wastes time on her nails (yes, getting dirt out from under the fingernails is nice, but I think nail polish is unattractive, as is makeup). Great outfits don’t impress me. Botox? Really? That’s difiguration.

    Losing weight might be nice and I probably would notice and mention that (I’d rather be around an athletic woman than a princess), but I’m seeing in this description of a superficial, artificial woman who wouldn’t be any fun to be around.

    I think that a lot of women think that this impresses a man. I think most men would rather have someone fun and relaxed, rather than someone who is this hung up on her appearance and would make me feel like I have to take her to a Presidential Inauguration or a $500 dinner at a 5-star restaurant to have any fun.

    I’d rather meet her in sweats. Or jeans.

    And please, perfume makes me want to gag.


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