I decided to re-write this blog post because it was one of the single most popular articles I have ever written.  As I noticed how many reads it was getting everyday I decided that I hated it and wanted to redo it.  Until I got divorced,  I was completely unaware of the realities of dating in New York city after age 35.  It is tough out there, for both genders but it is especially difficult for a divorced person.  Going out on dates is nothing like coming home every night to a spouse.  I think the original piece was so popular because there are so many lonely people wondering why something that seemed so easy when we were younger is now next to impossible.

When I was in my twenties, dating seemed so much easier.  Men and women didn’t have such exact standards, long-term compatibility issues weren’t discussed and everyone seemed so much charmed by each other.  I see it now in my friends who are about 10 years younger than me.  There is a look of hope and optimism in their eyes that is rare in most of us pushing 40.  Even if they have had major heartache,  a younger person is less likely to have had the soul crushing experience of a divorce.  And very few 25 year olds have had long-term relationships, most are simply too young to have had dated anyone for 10 years or more.  People in their twenties are generally more innocent and less jaded, so they are willing to take more risks and have greater hope in another person.  Then ten years later they get divorced, or break off a long-term committed relationship and end up single again and soon discover how things have changed.  When I go out with age appropriate men I find that for some of them,  everything becomes a deal breaker.

Deal Breakers

  • Undesirable neighborhood
  • Lives too far away
  • Occupation
  • Past marriage or marriages
  • Social group or friends – not compatible
  • Pet allergies
  • Drinking habits – or in my case that I am not much of a drinker
  • Diet, exercise habits, hobbies etc.
  • A date reminds them too much of their ex.

I have to admit I do it myself, I am no longer so idealistic or starry-eyed when faced with a potential mate.  When I was 25 I could see myself dating someone who worked in a bookshop and had ambitions of becoming a playwright.  Now if I meet the same man at age 38 I am more concerned about why he hasn’t gotten his act together.  If he has had plays produced then that is one thing, but if he is still dreaming of the “day” when this will all happen I can’t really take him seriously.

Personality Problems

  • Socially awkward to the point that they have extreme difficulty connecting with others
  • Too selfish and self-centered and have never had a long-term relationship
  • The type of person who doesn’t want a relationship and wants to stay single
  • Severely damaged from past relationships
  • So set in their ways to allow another person to become a part of their life
  • A serial cheater or abuser who goes through partners like kleenex
  • Too immature to have a relationship


To some men, once women hit their late thirties they are simply less desirable because they are less fertile.  It is especially frustrating for me as I have had multiple female relatives reproduce without extreme medical intervention into their forties.  What makes things even more difficult is that many men and women in their late thirties have children from a previous relationship.  So one partner might be completely finished having children and never want more, while another partner is desperate to have children of their own.  And of course compatibility issues arise with a new partner if the partner does not get along with their children.


Generally speaking as we get older our jobs and lives get more demanding, not less.  So the man who worked in a bookshop in his twenties is now working at a publishing house pulling 60 hours a week with staff underneath him.  Everything is more complicated and the free time needed to nurture a new budding romance is almost nonexistent.   Or if one person keeps nontraditional hours, they will have a difficult time trying to date someone who is 9 to 5.

I now totally understand how a 45-year-old can look into the eyes of a 25-year-old and think they have found heaven on earth.  Sure they won’t have much in common and the age difference may eventually drive them apart, but instead of seeing a realistic mirror of themselves back they see a romantic ideal.  The younger person is simply less likely to see huge compatibility issues before they start.  How could that not be intoxicating?   Of course there are always exceptions, with wise 22 year olds and total naïve idiots who are 50.  I don’t mean to brush with that broad of a stroke, but there is a reason the average age of marriage in the United States is 27 for women and 29 for men.  The late twenties are the perfect time to start a family and to build a life, and still be idealistic enough to think that it will all work out.

A depressing as all of this is, I must find hope.  Before I would get wrapped up in someone knowing very little about them only to discover they weren’t right for me.  Now I have age and experience, I know what kind of man I am looking for and what I can offer to a new partner.  The problem is finding that other person.  Armed with a microscope instead of a rose-tinted lens I am more likely to make better choices for myself.  It just makes finding that needle in a haystack so much harder.

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51 comments on “Dating After Divorce – Why is it so difficult in your late thirties?

  1. Dillon

    Dang, I’m not your type: not much on children, too young for you, and less than 30 cats is a dealbreaker. But I do wish you the best of luck out there. It’s good that happiness isn’t dependent upon whether or not someone is or isn’t in a romantic relationship. As I’m sure you already know, relationship come with there own sets of difficulties, especially after “honeymoon” phase fades.

  2. Lori

    Enjoyed your piece! I love the “Baby momma math.” I can totally relate!

  3. Dave

    Great writing. I’m a single dad (1 son, aged three and a half) and a widower, living in NYC. I’m a 36 year old Australian. I have lived here for 4 years. As I’m a research engineer I mostly work with men, and having my son means I rarely have time to socialise without meticulous planning and expensive babysitters.

    I already have a child. Would I like another? I don’t know. Would I like a future girlfriend/wife to want to be a mother (or at least mother figure) to my son – absolutely.

    All this means that a cost-benefit assessment comes into play whenever I meet a woman I like. Is this a “casual” thing? Bzzzzt, nope, not interested – can’t spare the time or the hassle. My life means I can’t just keep seeing someone and not let my son meet them. But it’s so hard to know when you just met someone if they’re a good bet. It takes time which I don’t have to date them and find out.

    So how to date? Damn it, it’s so hard in this town. I’ve weighed up heading back to Australia but frankly my career is great, I love this city, and my son is growing up in America where he was born and where my social network resides.

    So more power to you Juliet. You may not find your soulmate but don’t focus on that. Just be open to those around you. Live life and love hard.

    1. Kate

      Hi Dave,

      Although I see that you posted some time ago, I was struck by your post and wondered if you might be interested in corresponding?

      — Kate

  4. Yep

    Hi, I just turned 36 and it hit me like a bomb. I don’t live in NYC, but I always imagined dating being easier in a place where there’s at least OPTIONS. I live on a tropical island with the social aspects of a small town. I am not sure about my current partner at all, but do I have time to find another that would be ‘better’? No idea! This is a difficult time for women who haven’t had luck or good relationships. I too am divorced and it took me so many years to get over it. The best way for me was to fall for another guy, only now I am heartbroken over that one! I just shifted the pain, I guess. My sex life is terrible, but the guy I’m with would be a good teammate and possibly a decent parent, too. I would hate to ‘settle’, have my baby (if possible), then meet a new person that would have been a better match. My advice to you is… take a deep breath… be as clever and as assertive as you can be for a number of years, then if it doesn’t work out, smile and realize happiness indeed is not dependent on whether you can start a family or not. I am going to give it my all and just figure out what to do. The worst thing is not knowing when your fertility would end. I too look way younger than my age, I generally get estimated 25. A lot of younger guys hit on me, who see kids as a thing for the future. It’s so easy for guys isn’t it? You just mate whenever you’re ready.
    I think you have your values in order and don’t worry about the psychiatric stuff, we all have that. You have to realize you’re probably just damaged in your self esteem still. You should just not focus on love and finding someone who can be your friend, then perhaps reveal your age and child wish in a later stage. Don’t panic (it’s hard, I know). Remember, stress can keep you from conceiving! Just relax, smile, be as happy as you can be and find the best places to meet men. Go up to them, chat, give them your email address right away, ask for friendship, etc. Just do it!!! be aggressive!! Most guys will be flattered. Start a dating site for the girls like us who want to meet their baby daddies and GET ON WITH IT! LOL. Good luck, honey and remember, adoption is a very beautiful and humane thing. There are many babies out there who don’t have anyone. I know how you feel. Try as hard as you can and don’t waste time on guys that aren’t worth it! You’re hot, blonde, blue eyes any guy would love to mate with you! Do what you gotta do… LIE about your age if you need to. Just take it as a case to case thing. This is much like a lottery isn’t it? You never know what your life will be like in 5 years from now. Big changes could be ahead. Try to enjoy this crazy time! That way you will attract the right people! This is worse than puberty isn’t it? The stress I am having from this almost makes me think I am menopausal at age 36. LOL. I don’t think I am though. I bet I can still have kids for a long time to come. I have taken the best care of myself inside and out for soooo long. For my future babies. GOOD LUCK and just be happy regardless, if you did your best. Don’t look back. I wasted a lot of time too, but then I would not be the person I am today and would not be able to be the great mom I can be today if it wasn’t for figuring out what works for me and what doesn’t.

  5. Yep

    Oops I meant ‘you should JUST focus on love’- typo sorry!

  6. Sasha

    Very interesting article, but I just want to add that dating while in your 30’s is fairly difficult no matter which city in the USA that you live in. I think a big part of that is many people in their 30’s still look for the wrong qualities in their mates. For instance, it seems that many men still focus on a woman’s physical attractiveness with little regard for her character. The same can be said of some women, except the object of focus tends to be his financial status. Additionally, some people just don’t realize that having things in common doesn’t imply compatibility.

    Good read.

  7. Anders

    Finding someone that can become ones spouse is not easy for anyone. Suggesting effective ways for someone else to go about this process is, if not futile and pretentious, a stumbling in the dark.

    I will nevertheless offer this observation.

    When you set out to accomplish something. The spoken or written word that you issue is the formulation of your vision.

    Stating what you desire is the most direct route to finding it. This goes for all things from finding your keys to finding a spouse. You would not describe all the keys that don’t fit your lock to find the one that does. Same thing with a spouse. What are the desirable qualities that person has to have ?

    Enter the priorities list. What is the most important quality the person must posess ? Priority ONE There is a patented answer for this — loving you —- Which is not equal to infatuation or beeing in love and it is a circular argument I know, but the fact remains this is the most important quality.

    All the rest of qualities, assign them a number. Low number high priotity, several qualities can have the same number. ONLY state POSITIVE qualities never a don’t or a NOT.

    When you state a negative quality with a NOT in front of it is the same thing as putting that negative quality as a desirable item. So ONLY use positive qualities.

    Keep the list short and sweet max 10 items and prioity from 2-5 give it a lot of though, re-examine and reformulate.

    Needless to say, patience, perseverance and common sense, is required.

    1. Elizabeth

      Hello Anders,
      I know you posted a while ago, but your points are still relevant and absolutely true and going forward, I will certainly apply them.

      Thank you

  8. Kiri

    The problem is that everyone, and I mean everyone, has their issues. And issues only become more entrenched as people grow older. A guy who’s the life of the party at 25 is a bloated alcoholic at 45. A woman who is “feisty” and has a “big personality” at 25 is a bitter wreck at 45. You get what I’m saying. And then because everyone has their issues, they also have their “red flags.” At 25, we simply don’t recognize them. In our 30s and 40s, we’re capable of saying, “Oh, that tiny thing he did on date two? That’s really going to blow up down the line.” You can see every flaw and incompatibility from a mile away. And since no one is perfect, you begin to try and prioritize: Which incompatibilities can I deal with and which not? However, if your life is relatively successful and happy, you may just decide you don’t want to deal with ANY incompatibilities, and may not wish to compromise at all. And who’s to say that’s a bad thing?

  9. exactly right says

    i am a STRAIGHT MAN, and now meeting a GOOD WOMAN in my late fifties is very hard for me. i seem to meet women that are so VERY NASTY WITH AN ATTITUDE PROBLEM AS WELL. in my opinion, women are not looking for men like they use too. i hate going out as it is because it is a game that can’t be won, and women have become really HARD just to start a CONVERSATION with them. since i live down the SHORE, i certainly seen my share of very nasty women, especially that many of them today THINK THAT THEY ARE ALL THAT NOW. what LOSERS many of them have become today.

    1. julietjeske

      Well I don’t know you, but I assure you it is also difficult for women your age too. It is difficult for everyone, I think that is why there are so many books, websites and dating services out there, as so many people are frustrated and fed up. Hang in there and try to keep a positive attitude, or at least if nothing else cherish your friends. That is what I do now, I just focus on the relationships that are working in my life instead of the ones that aren’t. But it’s hard out there…that I would agree with you 100%.

  10. exactly right says

    to julietjeske, it is very hard for us MEN that are very serious about meeting a GOOD WOMAN. i had been married at one time, and i was a VERY CARING AND LOVING HUSBAND, and very committed to her as well. i have to say that, i was the ONE WOMAN MAN at the time. i even thought that i was going to have a FAMILY, but that never happened. she had the nerve to tell me that she wanted an open MARRIAGE, and that is when i went for the DIVORCE. i am not really into the BAR SCENE at all, since there seems to be so many women today playing games. the way i look at it, god seems to make many men and women VERY LUCKY ENOUGH too meet one another, and others like me not so lucky at all. i do have to say that the men and women out there that have each other now, should really go to CHURCH and pray and CERTAINLY THANK GOD, especially that many of them have a family. it is the men like us that are REALLY HURTING NOW, and would have wanted the same thing. now single and alone again, really sucks for me. but i will go out EVERY SINGLE NIGHT, SINCE I HAVE NO ONE TO STAY HOME TOO. now i will just go out, and hope that i will be at the RIGHT PLACE AT THE RIGHT TIME, to meet a good woman for me this time around. thank you very much for your support, and GOOD LUCK to you too.

  11. talktala:_ kathleen

    Reblogged this on talktala:_ and commented:
    Here is the spectacular Ms. Juliet Jeske. She gives her two cents on dating after divorce. We thought this was an authentic voice for everyone out there going through the same thing.

  12. Daniel

    honey, at your age you can’t afford such a long dealbreaker list…

    1. julietjeske

      Well you completely missed the point. I am actually saying the complete opposite. Men in New York, find the list of deal breakers in regards to ME. So I am not the one with a list, they are. And you are probably older than me, the last guy on this blog who tried to call me old was 20 years my senior.

    2. julietjeske

      And just to drive my point home, here is the quote from the article…When I go out with age appropriate men I find that for some of them, everything becomes a deal breaker….followed by a list of deal breakers.

      So how the hell am I talking about some list I have? You missed a couple of words there, and completely misunderstood the sentence.

    1. julietjeske

      It was implied…Honey at your age you can’t afford such a long dealbreaker list.

      You don’t know me, so you have no place calling me honey.

      And again you completely misunderstood what I wrote. I don’t have a dealbreaker list, never said I did. In fact I said that SOME guys that I have gone out with seem to have one, I am sure some women do too, but I didn’t write that. If you post again…I delete everything. I don’t put up with harassment or abuse on here. I am sorry you misunderstood my article, but was is actually the most popular article on this blog in 2012. I have about 135 and this was #1. I am 39 by the way.

  13. Panty Parade

    Thanks for the pingback. I get the feeling we’re writing the kinds of books single women really crave. The segment you picked is central to what I’m writing.

    Happy writing!

  14. Ares

    Spot on…but it’s like this all over the world.

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  39. Kenedy Singer, Ph.D.

    Dating at any age can be super tricky. The passion of chemistry is awesome. Without it our species probably would have fizzled circa the era of the caveman. However, truth be told once those darn hormones normalize after the immediate rush of the newness wears off many relationships go into shock. We ask ourselves WTF am I doing with this guy? Well, it was “the chemistry.” The chemistry didn’t tell you though that this dude leaves the toilet seat up, doesn’t care about others, lacks ambition, and quite possibly could win a Darwin Award. So, what to do? Jump ship of course. Next time around though it’s much better to ask more questions and take more time before jumping in the sack and sealing the deal.
    I see with my clients all the time how small gentle tweaks lead to finding the man of their dreams.
    Good luck in love,
    Kenedy Singer, Ph.D.

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