Dating After Divorce At 50: What To Wear, What To Say And Other Tips

dating after divorce at 50

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

When I was 49 years old, I ended a six year relationship. Single again at 49 and dating again was nauseating to think about, but I did it. Is dating after divorce at 50 easy? Um… How can I say this delicately?


That said, there are many many benefits to dating after divorce at 50! Soooooo many!! It’s really fun and you definitely care a lot less about what people think of you.

Despite all the baggage and the tainted outlook some people over 50 have, I think people dating after divorce over 50 are so much more authentic, interesting, real, funny, wise, and entertaining!!

Please look at dating after divorce at 50 as an adventure versus dreading it. A positive outlook changes everything.


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So, with that said, here is some of my dating after divorce at 50 advice. I decided to break it up into four  categories, and offer in my opinion—based on my history of dating and relationships, what is attractive and what is not. Remember that what I wrote is just my opinion—not what is right or wrong.


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Men, vests will never be attractive to a woman. We love classic button downs, jeans, khakis and understated attire. That doesn’t mean boring. It just means showing yourself and your body to a woman rather than meaningless designer labels and what you think will be impressive.


As far as the way a woman dating after divorce at 50 should dress for a date: I truly believe that men don’t want the low-cut, cleavage-showing top, the skin tight jeans, or the 5 inch heels. The key is to be sexy without trying.

That comes with wearing clothing that highlights the parts of your body you love. If you have great legs, go with a skirt and heels. If your lips are your thing, bright lipstick is the way to go. If you are proud of your biceps, go sleeveless. Whatever outfit is going to make you feel beautiful and convey the most self-confidence you have, that’s the outfit.

On a side note, in regards to perfume (or cologne), less is more!


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Here are 9 huge turnoffs:


1. When someone talks about how great Bumble or Tinder has been to him or her, and how tons of men (or women) are dying to meet them. Even if it’s true, keep it to yourself.

2. When people lie and talk about how much they are enjoying meeting new people and how much fun dating is. No one loves it—at least for more than a couple weeks.

3. Badmouthing an ex or using any derogatory terms when referring to him or her. I once went out with a guy who called his ex-wife a “C” and I almost spit up the sip of wine I had just taken. I wanted to leave before dinner. I would never give him the time of day again. Ever.

4. Bragging about a job and how well you are doing. You might be thinking your date will feel good about the fact that you have money, but I find those who are truly successful don’t really talk too much about that.

5. Playing the victim or having the woe is me attitude. It’s very unattractive. Feel sorry for yourself to your friends and family or therapist, not your dates.


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6. Giving someone a novel about your life instead of asking your date questions and allowing that person to talk about themselves. In dating, listening is so much more important than talking.

7. Trying to prove you are the best father (or mom) in the world and talking about how much time and money you spend on your kid, or how little time or money your ex spends with your kids.

8. Sending food back or being rude to the waiter/busboy.

9. Looking at your phone and texting. Phones should be in your purse/pocket for the entire date with the exception needing to see it in case kids call.


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The winning attitude:


1. Smile a lot.
2. Laugh a lot.
3. Before you leave the house, think to yourself, “Whatever happens is fine. If he/she doesn’t like me, that’s OK. It doesn’t mean I’m unlikeable. It just means it wasn’t a fit and wasn’t meant to be. I still like me.” Also, remember that you are there to see if you like that other person, so focus on that more than whether that person likes you.
4. Don’t be afraid to be vulnerable. I once had a guy tell me I was the most interesting first date he’s ever been on. Why do I think he said that? Because I was asking some pretty deep questions early on and the conversation got pretty interesting quickly.
5. Remember that if you like yourself, he/she most likely likes you too. One way to tell if he/she has potential, is if you like yourself around him/her. I once dated a guy who I always felt not good enough for—for reasons I will never, ever know to this day! I wanted him to love me so badly and he just didn’t. I should have broken it off after the first date instead of torturing myself for a few months. Not really sure why I did that to myself.
6. Make the other person feel important, special and like he or she matters. Even if you know it’s not a love connection, listen and be interested in what they have to say. You can never go wrong treating someone with this kind of respect.
7. Level with your date. Don’t be afraid to be upfront about what you want. Of course, you don’t want to scare the person off, but don’t play games. There’s no time for that.




At the end of the night


1. Don’t have sex on the first date. Look,  I know a few people who are married to people they slept with the night they met them. I respect that, but I think that’s rare. I think it’s a bad idea to have sex on a first date. Why not talk and kiss and laugh and giggle and really get to know someone before taking off your clothes? Sex too early on causes clouded judgment and people end up thinking they’re in love because of the sex. If you wait, the love is authentic.
2. Don’t ever go to someone’s house or get into his or her car if you just met the person and only know them from the dating app or site. Wait a few weeks.
3. If he doesn’t call (or she doesn’t respond) even after you thought things went well, chalk it up to the typical disappointment that dating can bring, and don’t ever ever take it personally. You have no idea what’s really going on in that person’s life.


Advice for: I can’t meet anyone in dating after divorce at 50

I know a lot of people who date and date and date and none of the dates ever seem to work out. Or, they say “I just can’t meet anyone normal.” They are perpetually single and when I think about why, I can think of a few reasons.


1. Bad luck—just not in the right place at the right time.

2. An attraction to non-committal, bad boy types.

3. A dislike of themselves. It is impossible to fall in love if you don’t love yourself.

4. They are carrying too much pain from a past relationship and don’t have the insight to see that they need to dig deep (by that I mean therapy) to find out how to heal and fix themselves first.

5. They rush the relationship and things become disappointing and awkward so it ends.

6. In this day and age of people at your fingertips every minute (Tinder, Bumble, etc.) it’s like being in a store with so much merchandise that you can’t really shop effectively. You miss some of the good ones.


In closing, no one who wants to be with someone should have to be alone. It saddens me when I think about lonely people, and I have been there myself in the past. Just remember that there is so much you can’t control when it comes to dating after divorce at 50, and relationships after 50, but you CAN control the person you are.

So, that means getting yourself in the best possible shape for dating. I don’t mean physically, although if that’s what’s going to make you happier than OK. But what I do mean is, getting yourself mentally and emotionally healthy so that your dates are getting the best you. This will improve your odds of finding love.

Like this post? Check out, “There are no Buts In 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:

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