Over 40 and Single again: 4 Advantages in Starting Over

over 40 and single again

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

 The year I turned 41 was interesting, to say the least. My ex-husband had moved out a month earlier and we were just beginning the divorce process. What’s it like when you’re over 40 and single again? I’m going to tell you.

“I’m over 40. Who’s going to want me??”

My ex already has a girlfriend and I haven’t been on one date in over a year. Where’s the justice in that?”

 “There are so many wonderful, smart, beautiful divorced women out there and all the men are either drug addicts, alcoholics, psychos, control freaks or cheaters. You do the math.”

  These quotes are some of the things divorced or separated women have said to me in the past. Finding myself over 40 and single again was not fun. Not only was I going through the pain of my divorce, mourning the failure of my marriage, dealing with my two young children feeling sad about daddy moving out, and worrying about finances, but now I had to go back out there into the nightmare world of dating?!


Alyssa Dineen -
Online Dating Coach and Stylist


Yikes. It was scary. And depressing. And horrifying at times. I had a few situations that were so unbelievable, that the stories ended up in my novel, FREE GIFT WITH PURCHASE. And there were times I seriously couldn’t believe why God would keep sending me loser after loser after loser.



But, I have to be honest, there was an element of excitement to being single. After all, I was starting over. I was getting a second chance at happiness. I was leaving a bad, bad situation that brought me to tears for years before I officially got separated. I was getting away from a marriage that wasn’t making either one of us happy, and I was moving into the unknown. And the unknown was semi-attractive, in the sense that at least it wasn’t “the known” which was constant fighting, misery, fear, sadness and loneliness.


So, into the unknown I went, and now it’s years later. Getting to the point where I am today, however wasn’t easy. It took:


1. a lot of self-introspection
2. the guts to admit my faults and my insecurities
3. hard work to get myself where I want to be professionally
4. learning the single mother life and how to put my kids first above everything, no matter the price.
5. taking time to be alone/not dating anyone and feeling like I might die of loneliness at times
6. making mistakes and fessing up to them and not being too hard on myself
7. getting myself to eat healthier and realizing the importance of good physical health
8. learning how to accept and let go of anger and not become bitter
9. courage to face life alone.


Vestor Capital


I realized I was the leader of my little family, and I had to take the role as the rock solid one, the go-to person, and the one my little kids could depend on 100% all the time. And honestly, the responsibility feels good. It gives my life purpose and meaning and joy that I can’t even begin to explain.

So, with all that said, that is the first thing on my list of 4 advantages to starting over at 40:


1. Being responsible feels good.

It feels independent and it gives you self worth, self-confidence, and self-love. It makes you feel like your life is really meaningful because you are so needed. No one is taking care of you, and others need YOU to take care of them. You matter immensely.


2. You’re starting over but you’re better equipped.

In other words, think about when you started dating, around age 18 or so. Think about how clueless and naïve and how hurt you got when it didn’t work out. Think about all the mistakes you made with men because you were young and you just didn’t know. Now, my girls, you are going into battle with heavier armor, (and by heavy,  I don’t mean pounds, I mean more knowledge and experience!) You’ve learned, you’ve made mistakes,  you know what to look for, you recognize the red flags, you’re smoother, you’re smarter, you’re wittier. You’ve got it goin’ on!  Show him the goods!


My Divorce Solution


3. The clock isn’t ticking to get married and have kids, so you can just have fun.

I can remember being panicked in my 30’s, wanting to have kids so desperately and feeling like I would never meet anyone in time to have that happen. Well, guess what? I have my kids and I wouldn’t trade them for the world. And now, all I have is time. Time to have fun, time to enjoy myself, time to get to know interesting people. And that’s a beautiful feeling.

One thing I see that bothers me a lot is when men and women whose ink on the divorce papers is still drying, and they are getting married again. Maybe it’s me, but what’s the rush? You were just married. You see how that went. Why on earth do you want to do it again so quickly? Breathe. Enjoy being by yourself. Learn to appreciate it. Don’t be afraid to NOT be married.


Our Family Wizard


4. You are more secure in your own skin.

This is a true story. I was at a bar about a year ago with my girlfriend (who is my age) and we started talking to these young guys who looked like they were in their 20’s. We weren’t flirting. We weren’t trying to pick them up. We were just chit chatting. Their girlfriends walked into the bar (about the same age as the guys) and I instantly got the sense they felt threatened by us. I seriously could not believe it. They were so insecure and rude and territorial with their guys. If I were them, I would have been thinking, ‘Oh, these older ladies are so cute.’

Being older means feeling more secure in your own skin, highlighting your outer beauty, and doing your best to look your best physically. But, it also means realizing that what’s inside is so much more valuable, and if you have self-confidence and self-assurance, and you hold your head high, your shoulders back, and walk with pride and grace, I think that really comes across when you are meeting men.

Like this article? Check out “Dating Over 40? 15 Reasons Single Men Prefer Us”

Listen to the Divorced Girl Smiling podcast View the DGS trusted divorce professionals! Divorced Girl Smiling is now offering a private, no-cost, one-on-one phone consult

Sign up for the Divorced Girl Smiling newsletter to get articles on divorce and dating.

Sign up


    Divorced Girl Smiling welcome video
    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: DivorcedGirlSmiling.com

    22 Responses to “Over 40 and Single again: 4 Advantages in Starting Over”

    1. Simon Solomon

      Another terrifc article that I can totally relate to. I’m living this scenario at this particular time in my life and reading these insightful blogs helps me stay grounded to reality. It’s a tough dating world out there these days. Thank you Jackie for the clarity you bring to the topic.

      • J

        While the article is encouraging and I can totally relate to the author, she starts it off on the wrong foot immediately. Stating, that maybe this is her (and many others) second chance, she follows up with “There are SO MANY MEN that have this problem or that one, etc.”. If you think that, you will always in your subconscious mind be on guard and have one foot out the door. The good guys that are out there that are single and want to be their best for you will always sense that. It shouldn’t be a case where someone is always having to “win your love”, there should come a time that you accept that YOU aren’t perfect nor is anyone else going to be. Divorce hurts, getting cheated on hurts, being abused hurts, no so does being taken for granted. So, while you are single again don’t look for someone to sweep you off your feet. Those guys are short lived. Instead, look for a guy that has his stuff together (job,home,healthy,responsible) but that is consistent. If you find a guy that is consistent, he won’t always know what it takes to “win your love” all the time. However, he might just be that ordinary guy that you see in the restaurant eating by himself night after night, week after week. He’s consistent, he has a lot to give, but he’s also old enough and mature enough to stay away from women that can’t be content with what he can give so he stays single as well. Many women today want their cake and eat it too, but in reality a good man isn’t always going to be exciting AND he may have an issue or two as well. One thing is for sure though, he will be consistent, you can count on him, and could be the best thing you’ve been looking over all this time while you’ve been wanting your new adventure and a guy like the one in the romance novel you’ve recently read.

    2. mikey

      Great article! Great blog!
      They read a study on the radio the other day that asked men and women at what age are women most physically attractive and just attractive. The answers came out to about 32 for physical, but 38 for attractive in general. I think that just shows how confidence and wisdom are.

    3. ajc

      Thank you for this article. I have just recently split up with my husband after 7+ years of marriage. He was a MUCH younger guy, and for the most part, I don’t regret our marriage because I deeply loved him for a time, am sure he loved me, and I still care a great deal about him and will probably always consider him one of my best friends. We are just…not good together. Still, now I find myself at 43, with a daughter who’s gonna be moving out in a couple years. I’ve never been one to go out much, if at all, I don’t have a huge social circle (most of my friends are “cyber people” I only know online), and I am out of shape and not very physically attractive. I was a single mom before he came along for 9 years, and I had resigned myself to being single then, but now that I’ve had someone, I am terrified of never being with someone again, never having someone to kiss me goodnight or hold me on his shoulder while I’m falling asleep. This article is empowering and encouraging in a time when I really need that, and I thank you for it.

      • Liz

        Ajc, this sounds like my life. The much younger guy, feeling unattractive and out of shape but even worst because I had 3 kids with youngster….lol It’s awful when my 3 yr old cries for his dad but he’s an alcoholic and in 6 years we are going no where. He brought out the worst in me and we had nothing in common. It will be so hard for me to find someone because I’m also a burn victim. I don’t know if I’m terrified or relieved. I worry so much about the financial situation. I wish you the best of luck.

      • Avary

        ajc, if you are there, please chime in and let me know. I have some questions for you after all this time.

    4. Debbiedoesdivorce

      This blog/s are so helpful in building back our “self-worth” . I just have to thank you for your “makes perfect sense” inspiration. I’m 46 w/ a 4yr younger husband and a job as Mngr at a local well, let’s just say I’ll never be 20 something again (as if I’d choose to) or fit into xxsmall orange short shorts makes it blatantly obvious he’s now far too young for my goals and priorities. I’m afraid of this 2nd divorce (1st only 3yrs huge boo boo) but I feel a little excited for what is up ahead! My boys are grown and wouldn’t be too disapointed in our parting ways. I’m only gonna be burdened with one “not married responsibility” and that is taking out the trash. I can do this with so much more enthusiasm AND grace! Thanks for your input/direction!

    5. Caspar

      Your writing is very real and from the heart. In particular the 9 points you make about your 7 year journey to get to where you are now. I always think its useful to know where you are going and what direction.

      The statement ..”life is xxxx” always brings me back to a reality check and then from there I can decide what I’m going to do next. In my case, “Life is an audacious daring adventure”. Clearly this will be different from person to person and what they believe in. Whatever that compass is will dictate how you approach things.

      So, for me, dating at 42 is an adventure. It’s an opportunity to have fun, to connect with people and to enjoy life. One of my mentors always asks the question – is this the beginning or the end. If you always see it as the beginning, you’ll have a whole different experience than if you see it as the end. Life really is just beginning no matter what age you’re at. Today truly is the first day of the rest of your life. You were put here to enjoy life. Have fun : )

    6. Teeny

      I am a single mom of a 16 year old and a 2 year old. My 16 year old is from my first husband and we have a great relationship. My 2 year olds father and I broke up a week before our son turned a year old. About 6 weeks after we split I found out he was having an affair with my younger sister. They are still together and it had pretty much shattered my self confidence as far as dating. I had my youngest a week before I turned 40 and I had gained 60 lbs mostly due to being high risk and not being able to work out. Now I am 42 and single and have no time to work out and I am completely intimidated about dating. On the up side I have a great job and I totally financially secure! Own my own home and take great care of my kids. Any advise?

    7. jenny

      I’m very worried about my marriage. I don’t know how to stop things from spiraling out of control. I have 3 children at home living with us. I know they will be devastated when it ends inevitably it is going too. My husband of 14 years longs to make sure he isn’t wasting more time with me when he could be happy with someone else. I just don’t know how to start over. I I guess the good thing about it is I am financially stable, still in on shape. I would be worries about all the weirdo in dating game too.

    8. michael

      I am a 52 year old man who has been single for 18 years , never heard about your book ! I try to date but with little success I have every thing I want except a women to love and spoil ! my marriage failed because my ex after 12 years together and a 8 year old daughter who wasn’t mine found that out during the divorce and also that I cant have children left me for a women :-(.So don’t give up girls there are guys out there that can give you the love you are dreaming about and can love your children like they were there own just don’t let you emotions cloud you good sense also’ its all right to be single even though I believe that we were all made to be with someone ! we all come with baggage for me there are three basic parts to a relationship financial ,physical and emotional its very rare to find a person that’s a perfect fit in all respects; so size and shape don’t matter just a desire to b together.

    9. Smiling

      Enjoyed your article. I’ve been divorced for almost eight years now and have poured all of my energy and time into my 3 children, 22, 15 and 12. I constantly think reflect on who I am as a 44 year old woman. I haven’t dated at all and do not even know how to get back put in the dating scene. Thank you for sharing your experience, it helped me to realize that many share my experience And self discovery is fantastic! One day I plan to date again but for now thanks for sharing and hearing the voice of so many divorced single parents. It’s helps to know we are not alone

    10. Rosie Lively

      I am a single mom of three and just went through a divorce. I am about to turn forty and I’m worried about not working again. Would you please send me your book pro bono?

    11. Ellie

      Wonderful article. I am 40 and just ended a 5 year relationship, previous to that I had a long relationship with my children’s father. I havent been single I over 20 years. I have 3kids, all 16 and over, and I feel like I was living the cliche of life begins at 40, it actually feels like that for me. I found it hard for a year, being single, huge adjustment. But I rather see this as a gift from God, my children are older and in work or college, no man to answer to, good health and fitness, a new start. I’m grateful.

    12. Rob

      I don’t understand why single, or divorced people, believe it is a necessity to get into the dating scene. Sure the company could be nice, but it’s not a requirement. Wanting it, and not getting it, just leads to misery, so why bother?

      • Jackie Pilossoph

        That’s such a negative way to look at it. It’s not a necessity to get into dating, it’s a choice. If you go in with the attitude that there are no guarantees, and just try to meet nice people who you enjoy, then if love is meant for you it will happen. People who are fulfilled in their lives and surround themselves with people they love are OK if romantic love doesn’t happen right away. The key is to focus on your own life and what makes you happy–professionally, personally, and with people you enjoy and love, and let love just come to you. It takes a lot of patience and faith, and it’s OK to cry if you are disappointed or frustrated if it isn’t happening.

    13. Paul

      Well with most women nowadays that are real feminists and men haters altogether, which the great majority of them are gay to begin with. And that makes it rather very difficult for many of us straight men trying to find love nowadays, especially when many of these type of women will Curse at many of us men for trying to start a conversation with a woman that we would very much like to meet. And i mean we really do get Cursed at for No Reason at all too since i had it happened to me already, and a few other friends that i know as well. Doesn’t make sense for so many women today to act this way, and it is very obvious why so many of us men are still single now unfortunately since we really can’t really blame ourselves either. Very risky for us men today.

    14. David Poe.

      if you think being over 40 as a woman is touge, be glad you’re not 73 years old, and male. It’s even harder. Most women feel that you can tell when a man is liying ,if his lips are moving.Some of us DO TELL THE TRUTH. I’m one of the truthers. Talk about lonely. I am very! I can’t get even a date for dinner. Women are so afraid of what might be asked of them after dinner, they won’t even that the chance. I don’t expect anything but company and convertion.( But we all know that that’s a lie , righ? ) It’s not what you think. Loneliness is not a gender thing. Ask the next single , older man you see sometime.you might be surprised. 😂 poecampershell3@gmail.com. xox

    15. Dor

      Good article 4 Advantages to Being Over 40.
      I was over 50 when divorced and that age had many advantages.
      I’m independent, knowledgeable, learned how to live on my own and enjoy my adult kids.
      I now can focus on myself, my friends, and decide what I want to do with my time.
      I raised my kids, I see them often and make an effort to text, email daily and call weekly.
      As far as dating, I’m in no rush. I attend Meeting ups and when I may find someone I’m interested in that will be good. I’ll never marry again and don’t see that need, as I did when I was 25.
      I’m grateful, and try to find something I enjoy doing each day.


    Leave a Reply

    Your email address will not be published. Required fields are marked *