Divorced Chick Gives Dating Advice to 20 Something Guy

If you’re a young, single guy in your twenties, who better to get dating advice from than a middle aged divorced woman? (me.) Think about why it makes sense. I can talk about the mistakes I made, I can tell you what I liked and didn’t like, both as a young women and now. I can ‘t tell you what to do, but I can tell you what’s worked for me and what hasn’t, what I enjoyed, what bugged me, what I would do over if I could, and…I can tell you about love. True love.

This is an email I received from a guy in his early twenties, who listed five questions to which he wanted answers. Here you go, cutie!

  1. Is it honestly worth getting married? I’m literally scared out of my
    mind after reading the divorce statistics.

It is worth getting married? Hell. Yes. I know I am the Divorced Girl Smiling and everything, but I happen to be a huge fan of marriage if you’re with the right person. Is it scary? Sure. But so was taking your first step, or moving in for that first kiss at age 13, or even having sex for the first time. But you did it and it worked out, right? Yes, divorce statistics are high. You have a one out of two chance of being divorced. But if you think carefully, and you really take the time to get to know her, spend time with her family, and really talk to her, your chances of it not working out will go down. Also, go with your gut. If it doesn’t feel right, don’t do it. Because if it doesn’t feel right and you do it anyway, you will be divorced.

2. Would you recommend getting a prenup?

It’s a tough call. There are so many factors to consider. I am surprised to see someone your age asking this question. I wish I had been as responsible as you are. When I was your age, that never occurred to me. I’m not sure I agree with this, but a friend of mine always says, “If you are considering getting a prenup, you shouldn’t be getting married.” He has been married for 20 years, so maybe there’s some truth to that. Also, he is referring to people getting married the first time. He might feel differently about second marriages.

3. Would you recommend online dating?

I’ve never tried it myself, but yes, I would recommend it. Just keep in mind that you have to have patience, and date a lot of women you might not be interested in before meeting someone you really like.

4. My biggest fear is that I’ll fall in love with a girl someday and invest
emotionally in her quite significantly. Then one day she might just stop
loving me and I’m honestly not sure if I’ll be able to cope with that
heartbreak and divorce… What would you recommend here?


Again, I can’t believe you are so young and asking this kind of question. Have you had your heart broken before? Are you parents divorced? There is something that is scaring you that I don’t think most people in their early twenties experience. So, maybe you should explore why you are so fearful and address it, and possible talk to someone—a friend or therapist? (or me!)

The thing I’ve learned about love is two things. First, there is no better feeling than “investing emotionally” in someone. Even if it doesn’t work out, falling in love is worth every pain. Secondly, love is about taking chances. “One day she might just stop loving me…” Of course you’d be able to cope with that. You would go on. I’ve had hundreds of readers email me and tell me they are heartbroken, that they are going through a fresh divorce. Months later, they will email again and tell me how in love they are.

What would I recommend? Stop being afraid and take a chance. Let someone in your heart. The most miserable people are the ones who because of fear never let that happen.

5. Is it possible to tell that you’ve met the “right” one? I’m kind of
afraid of being screwed over by either cheating/lying/gold digging women,
so are there any signs I should watch out for?

Again, who screwed you over? Who lied or cheated? A man in his early twenties most likely hasn’t experienced that (especially the gold digging part!) so what is it?

To answer your question, “is it possible to tell that you’ve met the right one?” Yeah. You’ll know. That’s what everyone says. Although, life is funny. You can second guess yourself, talk yourself in or out of anything. But the bottom line is, trust your gut. It is never wrong.

Lastly, signs to watch out for, regarding a cheating/lying/gold digger? People often say, ‘Listen to your heart.’ While I believe there is some merit in doing so, I’d say really think about the person’s character. What has she shown you? What is she made of? You know pretty early on. What are her values? Did she cheat on her last boyfriend? Is she a huge drinker? Is she materialistic? What are her girlfriends like? Nice girls? What’s her family like? Nice people? Normal? Is she loving and kind? Kind to others? Let yourself see everything. Being good looking and fun are important qualities, but if she doesn’t have this other stuff, forget it.


Hope this helped and best of luck!


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

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