Is Dating Different in Your 40’s?

I get SO many questions from women in their 40’s and 50’s who ask me whether my advice would work for them.

And I always wonder: why not?

Of course I understand that ageing is an anxiety that all of us secretly face and worry about, especially when it comes to dating. But does that really mean that the same rules no longer apply once we hit 40?

What is it about turning 40 that makes life so different? Is it that a 40 year-old wouldn’t flirt and go on dates? Is it that you can’t find good men once you’re 40? Is it that 40 year-olds live in some alternate universe where the rules that apply to 20 and 30-year olds no longer work?

Maybe I’m being dumb and naiive here, but I don’t believe any of those things. But I’d like to hear from you women on this issue.

If you have an opinion, ANY opinion at all about dating in your 40’s and beyond, please make sure you watch this episode of LOVELife and share your thoughts in the comments below. I’d love to hear from you.


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47 Replies to “Is Dating Different in Your 40’s?”

  • I am fiftyfabulous and use your dating techniques and they do work.

    If you want to find someone you definitely have to make the effort to go out and talk to everyone and any one it is a lot of fun and you meet some great people and some very special people along the way as finding someone is also a numbers game.

    I have several friends my age who have just given up trying to find anyone. I find this incredibly sad as there are a lot of great men out there wanting someone special too. We all have to fight the fear of not doing stuff or life isn’t worth living. I am not perfect neither do i expect the person I am dating to be either.

    Its been fun meeting the dickpic guys (well for 30 seconds , especially when he’s wrapped them in tinsel and baubles , well it was Christmas !!), the ones that are 50 plus never married and now want to get married and have babies (I really hope it happens), the ones that believe you are too old but they aren’t, the ones that say “you ‘re prettier than I thought you would be” (internet dating), the 32 year old (i am no Mrs Robinson), and the most special one of all …….the ones that think porn film sex is the way to go (it never ever is !!!).

    And then a man you’ve been friends with phones (not texts ) you and asks you to go out on a date…hurrah ! Exciting ….who knows what will happen, you just got to enjoy the day you are in.

  • There are certain “land mines” in dating in your 40s that aren’t really an issue in 20s/30s.

    I’ve never been married, so I have dated in all 3 decades (in my 20s, 30s, and 40s).

    In my 40s I’ve noticed there are a lot of men with multiple divorces (3 or 4 times divorced). Do I want to be ex-wife number 4 or 5? No. Next.

    Also, there are a lot of recently divorced men trying to rush into a new relationship. It’s very hard to keep first dates light and fun with this type of man. It feels like a lot of pressure to commit to him before I even know him. Next.

    There are fewer available men in my age group, in part because Generation X has a lower divorce rate than the Baby Boomers. There are many empty-nester divorced Boomers, and there is a huge population of never married Millennials, but Gen X is a much smaller population, especially in the college town where I live.

    As a Christian, I prefer not to date divorced men. It just makes me very uncomfortable. But… the never married population is generally much younger than I am, which isn’t morally a problem, but culturally there’s a lot of push-back. People *will* gossip and say cruel things (often the same people who are very tolerant toward gay couples will absolutely crucify a straight couple with an age gap where the woman is older – it’s the last bastion of hypocrisy).

    So, those are some issues that are different when dating in your 40s.

    1. And I should add, one important communication tip for dating in your 40s is: right after you ask him if he has been married before, and he answers “yes”, be sure to ask him “how many times?”

      My last bf (from over 5 years ago – I haven’t dated much since) was perfect for me – on paper. He was a year older than I was, he was smart, educated, decent looking, well traveled, kids were grown, he made a good living, etc etc. But… when I asked him how many times he’d been married he said 3, but technically the second marriage didn’t count because it had been annulled – the reason being he was still recovering from being shot in the head (in combat) and didn’t know what he was doing.

      I should never have agreed to another date after that, but oh well… Everything else seemed perfect! He was just nuts, and you can’t fix someone who is nuts, no matter how good they look on paper.

      I think I cut him a lot of slack for being a wounded veteran of Mogadishu, and I should have cut bait instead.

  • I have been single for years since my divorce 13 years ago and my last boyfriend dying 4 years ago. I have not had a relationship since and want to have one. Your tips on how to attract a man to marry and have children doesn’t apply much to me now that I’m 60, so the tips on how to lure a man by talking about making babies is ridiculous. I want a longterm relationship but I don’t want to live with the man. I am very busy but not too busy for a relationship. People seem to assume I just want sex or a hookup when that isn’t it at all. Also there seem to be men who want a wife, or a mother for their children, or want to play the field. How can I get through what I want? What words can I put on a dating site to describe the kind of relationship I’m looking for? Does the word companionship apply living together? What about the not very discussed topic of erectile dysfunction in men my age? Is this why men don’t want to have intimacy? I’ve run into it with both men I dated, and they won’t discuss it at all — one acts like all intimacy is off, the other didn’t seem to care if he gave pleasure. I want to please these men but they are not open. So I am moving on but what can one convey that indicates closeness without it sounding like sex or no sex?

  • Yes, I have similar situation like you, Anon. I am 40 and i am a virgin because I am a Christian. I was taught not to have sex before marriage. A couple of months ago, I met a 41-year-old guy online who is a widower with no children. He wants to have a complete family.He showed interest in me and we just clicked right away. We communicated through emails and apply Matt`s techniques on communicating with him. It actually worked well. We felt that we were right for each other and he does think I am a wife and mother material. However, my belief and the issue on sex become a big problem between us. He is a non-believer and he wants sex in the relationship because he thinks sexaul compatibility is very important in a marriage. I understand that. But then we stuck here. He worries that different beliefs will affect the way of raising kids since he wants children. And he worries that we are not young and if we find out we are not sexually compatible after getting married will lead to very bad consequence to me. He actually respects my choice of staying as a virgin and thought of different ways to deal with it. However, he lost patience and he now starts to distance himself from me and suggests me to find someone who share the same belief and the same view on sex issue. I think he is trying to not to hurt me. But i am afraid that i may not be able to find a guy like him. He has been so good and respectful to me. I am in a difficult situation. What can I do? I am confused.

    1. Its a dealbreaker for both of you. Find a man who doesnt mind, or even better respects, appreciates and/or shares your belief of waiting for sex after married. Im a guy and would prefer a woman who is waiting to give of herself only to her future husband. If the sex is not good initially after marriage, you work together to make it better because you love each other. Do you like someone for the person they are or how good they are at sex?

  • Hi Matthew~
    I am 41 and divorced, I also was in a long term relationship which involved my children, and living together etc. now I am single and do believe it is different dating at this age vs. when I was in my thirties only because life in general is an eye opener, “time” is not to be taken for granted and by now you are not only looking for what you want but have learned exactly what you do not want. I know personally I am not only thinking about myself and how a guy would fit with me but also my daily life with my kids and activities… can he keep up, will he accept it, etc. Also, I know at any age with dating there are steps to take but when we are younger we feel the luxury of time… to go out and have fun, to just get to know a person however long that takes, or maybe just being able to focus on that guy and the potential. As you get older you don’t want to “waste time” so to speak, knowing exactly what you want and having a guy know that is refreshing, it’s almost as if you skip some steps, is the chemistry there? is it ok having kids? do you want to be re-married or just looking to have the girlfriend? do they live on their own? All things that seem to be first or second date material sometimes even before you actually meet. So even though all ages of people have pasts and issues it is not so much that but how much time you are willing to go before “jumping in” together and the thought process of it just being about yourself & the other person to it being about children yours and theirs if they have them. At the end of the day happiness is key and we were not meant to be going through life alone. I do believe in the term soul mate and having that one special person you can call “home.” Btw love your advice… but going to flip the script on you, and was wondering what do you do to get the girl? Are you in a relationship and how would you feel about dating someone who had kids & had been married before? Assuming you don’t have kids and have not been married… would you take a chance or not?
    Thank you for your time,

    1. Hi Jennifer,
      I’m 46, been separated for 3 years from the husband, 1 kid and I agree with everything you say. Or in 4 simple words: I feel’ya sister! :-)
      All the best,

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