Dating After Divorce At 40: 13 Ways You Know He’s Loyal And Loving You

dating after divorce at 40

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

I got divorced at 41 and began dating shortly after. I have to say, dating after divorce at 40 or over has both its pluses and minuses, its ups and downs, and its highs and lows.

It’s a roller coaster ride! And, Dating after divorce at 40 can be really complicated. There are ex’s and financial issues and for those with kids, there are schedules and kids’ feelings to think about.  There’s also insecurity, self-doubt and baggage, all that make a divorced person a totally different “dater” than someone dating who has never been married.


There’s one thing I see in so many divorced men and women, and the best word I can use to describe it is indecisiveness. I feel like a lot of divorced people in the dating scene are all over the place. They just don’t know what they want. Some of them THINK they want a serious relationship, but when they get in it, they’re unsure. Some of them THINK they want to date around and just have fun, but then they meet someone, fall in love, and now they are completely thrown, and don’t know how to handle it.


Because of these scenarios, a lot of divorced people in relationships send mixed signals to the person they are seeing. One week they might be all lovey-dovey, the next, they might seem distant, aloof, perhaps.


Alyssa Dineen -
Online Dating Coach and Stylist


And that’s really, really understandable, and okay to a certain extent. But, what if you’re on the other end? What if YOU know what you want, but he or she doesn’t?


I can say this with experience in dating after divorce at 40 (and over.) There are certain behaviors in relationships that will make you sure he/she loves you.

Here are 13 ways you can be sure that the person you are dating is committed, loyal and loving you:


1. He’s constantly hugging and kissing you in bed. He Loves You.

The second you get into bed, he’s all about having sex. Maybe not.


Karla Kyte, Mortgage Lender and Certified Divorce Lending Professional



2. He shows an interest in your kids, and asks if he can attend your son’s flag football game. He’s in.

When you tell him about your daughter’s ballet show, he says, “Aww, that’s nice,” and then changes the subject. He’s not in.


3. You’ve met his friends and family. He’s digging ya.

You’re never been invited to a family get-together of his, and you don’t even know if he has friends. He’s not committed.


My Intuitive Health - Heal your Mind, Body, and Soul, in the Kitchen


4. He secures weekend plans with you at the beginning or middle of the week. He’s into you.

He texts you on Saturday afternoon with something like, “U around 2nite?” He’s horny.


Feig Mediation Group


5. You break your arm and call him from the emergency room. He drops whatever he’s doing and shows up within an hour. He’s in love.

You break your arm and call your sister, who of course shows up. You don’t tell him till the next day when he texts you. Your relationship is casual, at best.


6. You’re making love with him and the passion is so overwhelming you can barely breathe. It is at this moment he whispers, “I love you.” He’s madly in love.

You’re making love with him and the passion is so overwhelming you can barely breathe. It is at this moment he whispers, “You’re so hot, baby.” He’s madly in lust.


7. He says things like, “You have the best laugh.” He adores you.

He says things like, “You have the best ass.” He loves your body.


Miller Law Group - Changing the way people divorce


8. He shows an interest in your career, and listens when you complain about things at work. He loves all of you.

He has no clue what you even do, nor does he really seem to want to find out. He’s iffy about your love.


9. He introduces you to his ex and she gives you a look that makes you certain she knows the relationship is serious. He loves you.

He introduces you to his ex and she looks at you as if you are another number in a long line of women. In other words, it’s obvious she’s met all of his girls. No way.

10. It’s Christmas. He’s with his kids, but makes sure to see you at some point during the day and give you a gift. He sees a future with you.

It’s Christmas. He’s with his kids. You never hear from him the entire day or night. You’re his Saturday night girl.


11. It’s been the best year of your life, as far as love and romance. He makes you feel loved.

It’s been a really great year, but he has never said the L word to you. Deep down, you know the truth.


12. When you get to his place, you get in with the key he gave you. His love feels secure.

When you get to his place, you knock on the door and he yells, “It’s open.” He really likes you.


13. You ask yourself, “Does he really love me?” You look into his eyes and you have all the answers you need. He really loves you.

You ask yourself, “Does he really love me?” You look into his eyes and you’re really not sure. You just hope. He might not.


Remember that every situation is different, and it’s okay if you both aren’t in love. Dating after divorce is about making sure you feel good about yourself in the relationship and that you are happy. So, if it’s working, that’s great. But, don’t be afraid to face the truth. If you are in love and you know he isn’t, don’t settle by staying in the relationship, just because you are afraid you won’t meet anyone else. You deserve to have your love returned, if that’s what you want.

Like this article? Check out, “20 Things I Wish I Could Have Told My Newly Separated Self”

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:

    6 Responses to “Dating After Divorce At 40: 13 Ways You Know He’s Loyal And Loving You”

    1. Diane Herring

      I just started reading these and enjoy them allot. I am recently divorced going on two months now. I had a twenty four year relationship and was married 16 years out of it. I just want to say thank you for allowing me to read these it’s inspiring.

    2. Lillie

      I need some advice. I’ve been dating a single dad for 1 year. I have two boys myself. We’ve introduced the kids, slowly and its working well. Im friendly with his ex wife, in fact, we really respect each other. He treats me with so much respect, he is loving, kind and has invited me to family events. He makes time for me, and we have had an incredible year together. The only thing is, he has not said I love you, but his actions do. I am divorced, he is still finalizing his. I am in love. I am bursting to tell him, but Im waiting for him. Part of me is terrified that he doesn’t, but my gut tells me he just needs more time. Do I just tell him? I made a book explaining why I do and Im dying to give it to him. Do I just say “babe, I want to bring up the L word… I know how I feel, do you? Please help..

    3. Det

      Thank you. This helped me a lot . I fell in love with a divorced and thought he was in love me. Byt he managed not to talked to me and blocked me for 3 monrhs including chrustmas season. He unocked me on the 1st day of the year. Aftet reading this article i am niw sure he isnt really in love with me….

    4. Kimberly R.

      This article had some good points…but is very distasteful to me because of all the validation for sex outside of marriage.

      All the books I’m reading about Divorce say that is NOT wise. And, as a Christ-follower, I will not engage in sex outside or marriage. Heard the uber-expert Steve Arterburn’s colleague say it well this week, on the New Life Live counseling podcast: This would be “dangerous. That’s because it skews a person’s thinking about the relationship and creates a bond that is artificial and not solid or real or lasting (paraphrased).

      Another issue for me is that I thought these Emails were written from a Christian perspective, and sex outside of marriage doesn’t fit with the Bible.

      Is it just *some* authors of articles here are Christians?


    Leave a Reply

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