Is There Something Wrong With a Man in His 40s Who Has Never Been Married Before?

smiling attractive man

I’m currently speaking with a guy from Yahoo personals, he’s 42 and still single, never been engaged… This is a big red flag right? We have been talking for the past month and a half via the phone, I’m in Minneapolis, and he’s in Chicago. We have great long conversations, many that last 5 hours long, he’s commented how great our conversations are. He’s attractive too. How do I know if he’s just another “nice-player”? They are slick today. It seems many are online with no intention of getting serious… I just told him that it’s wild we have great chemistry but we could meet in person and realize that we are not physically each other’s type. To me, as naive as I am, I’d like to think he is not a “player” trying to work me over because we have these long conversations with a lot of depth to them. Our emails were very long to begin with too. Please give me some perspective and advice on this situation.

Dear Kate,

You’ve got four different questions going on here.

There is “How do I know if it’s worth it to try a long distance relationship?”

There is “I don’t want to be the victim of a nice-player in a long distance relationship.”

There is “I’m falling for a guy that I’ve never met but have talked to on the phone for 6 weeks”.

Is there something wrong with a man in his 40’s that has never been married? My answer is predictable: Yes… and No.

If you read the above links, your dreams will be summarily dashed – not because he’s necessarily a player, but because the odds of ANY relationship working are slim, the odds of an ONLINE relationship working are slimmer, and the odds of a LONG-DISTANCE online relationship are the slimmest – especially when you haven’t even, um, y’know, MET yet.

That said, the part of your question which really intrigues me is the “red flag” question:

Is there something wrong with a man in his 40’s that has never been married?

My answer is predictable: Yes… and No.

This is where I would make an argument that stereotypes exist for a reason. The unhealthy part of stereotyping is not necessarily the stereotype itself, but the assumption that ALL people in the category fit the stereotype.

Thus, if you have preconceived notions about gorgeous people, rich people, short people, gay people, Irish people, etc – those notions probably came from SOMEWHERE. They’re not pure fabrications.

Jewish people like playing Twister on the lawn is a fabrication.

Jewish people are often highly educated and highly neurotic is not.

Are we together on this one? Good.

So there’s the stereotype of the forty-something bachelor – and it’s a valid one. He’s a player. He’s a Peter Pan. He’s a commitmentphobe. He’s too picky. He’s emotionally unavailable. He’s a heartbreaker. He’s unrealistic.

All of those things are likely contributing factors as to why a man might be 42 and never married.

So now you’re faced with this very real dilemma – is this man a victim of circumstance, or is he the common denominator in all of his relationship failures?

But what if he was living with a woman for seven years who didn’t believe in traditional marriage? What if he was in a three-year relationship with a woman who cheated on him? What if he was once ready to propose and she ended up breaking his heart? What if he spent five years in a dead-end relationship and has had difficulty getting back out there? What if – god forbid – he made a bunch of bad dating decisions and just hasn’t met “the one”? (Hey, all of us want to think that about ourselves – let’s just say for argument’s sake that it’s true!)

So now you’re faced with this very real dilemma – is this man a victim of circumstance, or is he the common denominator in all of his relationship failures?

And I think it would be very easy, and coldly logical, to say BOTH.

This doesn’t mean you should enter into a relationship with a forty-something bachelor with the expectation of failure.

It does, however, mean that he didn’t become a forty-something bachelor by making great decisions in love.

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  1. 1

    Great article man keep on posting such great articles .wishes for your fyture.

  2. 2
    Karl R

    Evan said: (original response)
    “It does, however, mean that he didn’t become a forty-something bachelor by making great decisions in love.”

    In six months I’ll turn 40, and I’ve never been married. Self-confidence and marketability play a large role.

    Just over 3 years ago I was working two part-time temp jobs and earning less than $25,000 a year. Today I’m working a full-time salaried position and earning more than double that.

    Three years ago I was too skinny for many women (5’11”, 140-145 lbs). Since then I started excercising regularly and gained 15 lbs of muscle mass.

    Just over three years ago a long dry spell in my dating life ended when two women asked me out on the same day. Both were members of my church which I’d started attending 6 months earlier.

    Combined these things did amazing things for my self-confidence, particularly when dating.

    Three years ago my dating pool was small and rather static. Since then, I joined a yoga studio and started taking dance classes again. Now my dating pool is large and has a steady flow of new faces.

    During that time I also started reading dating advice, so now I have a better understanding of what I’m doing. And I’ve been dating constantly that entire time, so I have acquired more practical experience than I did during the previous 20 years.

    In some ways my life has changed as much as Sandra’s did when she lost 60 lbs.
    She’s entering the dating world as an inexperienced 23 year old. I felt almost as inexperienced when I resumed dating at the age of 36.

    I would agree that there’s a reason someone is 40 and still single. But it’s not necessarily a red flag.

  3. 3

    It’s unfair to make a judgement call on this guy based on superficial characteristics, but Evan echoed my sentiments. Really, you’re not going to know until you’ve met and spent some time with this guy. Yes, the risk is there that you will be rejected, hurt, etc. Your part is to treat him as kindly as possible and if he bails it’s his issue not yours. And even if he is/was a player, look at Warren Beatty. All it took to turn him into the picture of domesticity was Annette Benning. There’s hope for everyone.

  4. 4


    People look for dating “rules” to reduce their risk of being hurt.

    Dating rules don’t apply 100% of the time.

    Still, dating rules can be useful if you have an idea of how much the dating rules apply. If 7 out of 10 people over 40 who were never married are “relationship defective” that is useful information. You can decide whether or not it is worth missing out on one of those 3 gems to completely avoid hooking up with one of those 7 losers.

    The problem with dating rules is that there are no real statistics. The rules were made by dating experts based on their subjective and anecdotal experience. In other words, dating rules aren’t known. No degreed experts. No rigorous studies. No research.

    However, real research with real statistics has been done on divorce rates. It is known that over 50% of marriages in the US fail. It is also known that people who get remarried do not have lower divorce rates.

    In other words there is real evidence with real research and real statistics that divorced people are “relationship defective”.

    Can you imagine anyone, dating expert or not, advising people not to date divorcees in their 40s? I can’t. Those are most of the single people in that age range.

    Instead, dating experts will advise people to date that demographic, but be alert for warning signs. “What caused the divorce?” “If part of the cause was your date, has your date changed since his/her marriage?”. Etc.

    You need to come up with warning signs to look for in the man you are interested in.

    Is he a player? I don’t know anything about players other than that they want sex and nothing else. Common sense would dictate that with attractive women living all over the country that a competent player will not bother with a long distance possibility and that he will not invest a lot of time in a particular woman. Why should he? If he is only looking for a hookup he can get that at home and with less time than he has invested in you so far.

    I’m cynical about the prospects for long distance relationships so I would advise you on *that* factor alone to move on.

    When I date divorced women sooner or later I try to find out why they are divorced. Try to find out why your 42 year old never got married.

    Did he have a live-in “GF” for years and years? Was/is he a workaholic who had no time for his spouse ( this is ALSO the case with a number of divorcees, your dating alternative, who haven’t learned their lesson )? Does he have emotional baggage that prevented a marriage? Is he over that baggage? Sometimes people do get over things and become better people over time. FWIW, often divorced people, your dating alternative in that age range, also have emotional baggage. If not from their lives, then from their divorce.

    In the end, you just have to take a risk.

    Evan has a wonderful rule.

    Look at how s/he treats you, not at what s/he says and not what you want to be true.

    If the person is local, has been giving you everything you want in a relationship and has been doing that for a sustained period of time then s/he is worthy of your risk.

    If not, move on.

    1. 4.1

      That was a well written response and I think you gave some good advice.However to lump divorced people into a category by saying because their relationship ended, they are relationship defective, I don’t agree with. A marriage might have been a very positive relationship and raised a family etc and still end in divorce because people change over the course of their lives and decide to divorce. Many unhappy people stay married, so that doesn’t prove they are in good relationships or have better relationship skills.

  5. 5

    Another possibility: Maybe he didn’t believe in getting married just for sake of fulfilling a societal norm. Unlike say, his 42 yr. old counterparts who did. And subsequently found themselves divorced. Perhaps more than once.

    Maybe he didn’t want to take a vow to be with someone the rest of his life if he was unsure in his heart that he could keep that vow. Unlike his counterparts who took such a vow, believing they could always get a divorce if the marriage became untenable for whatever reason.

    Perhaps, just perhaps…he might be a more sincere and loyal partner than someone who married “to go along” with his partner’s wishes, or some other spurious reason. One thing we know, a marriage license is no guarantee someone won’t cheat.

    Seems to me, the only way to determine if a 40-something, never-married, person would make a good partner would be to get to know him/her IN PERSON. Then decide.

    1. 5.1

      Selena, I am heartened to know that there are wise, thoughtful people like you out there. Unlike the reader and author who make snap judgments without any factual basis.

      By the way, some of the “red flag” explanations – he’s too picky, he is unrealistic – apply just as much to women as they do to men. So if a woman hasn’t been married by 35 or 40, that is a big red flag and she also should be avoided or treated with caution, right? Women say all the time that they aren’t willing to settle for less than they want and deserve, whether they are being realistic or not. If a man assumes the same attitude, how is that wrong while the woman is admired for being empowered and independent? Double standard much?

    2. 5.2

      I really like what you had to say on here Selena. My parents met at college, married, and stayed married for 44 years until my dad passed away. My mom never remarried. I was ready to get married once, and had my world turned upside-down when that relationship suddenly ended to my surprise. I felt that I could no longer trust myself and my own judgement or be emotionally available again, after feeling like a total fool. I have friends and family who have been married and divorced, some multiple times. I helped one friend through a failed marriage, basically on suicide watch for weeks. I said when I was younger that I would only marry once. I am now 45, even though most folks are kind enough to say that I look much younger (which I partly attribute that to not being married or the stress of having kids).

      I am also very much a loner, and really only recently started to think about having a life partner. I guess I fit the Peter Pan or “super picky” category here, and have little experience in matters of romantic love, but I am only looking for one person. Your post at least lets me know that someone out there might also think there is still a chance for me to find love, even if I come with Red Flags! Thank you!!!

  6. 6

    I think you hit the nail on the head with the main concerns Evan. If a man that wishes to be married has not yet achieved that ‘goal’ by 42, it’s wise to find out if he knows why. The real question that comes in is whether or not you should automatically hold a person’s inability to reach their ‘goal’ against them. In this case I’d say you shouldn’t.

    I would, however, be interested in finding out if he knows the reasons why he hasn’t done what he wanted to do and if he is doing anything differently now to correct it. For example, if he claims to just not have met the right girl yet, is he doing things to meet more people that may be a match for him, etc. Understanding a situation and taking steps to correct it are key.

    My main advice to the letter writer would be to meet this guy as soon as possible. Don’t focus on reasons it may not work, etc. Meet and see if you even have the potential for a relationship in the first place.

  7. 7

    My take is that the farther the distance, the more difficult. A 5 hour drive or train ride isn’t as difficult as as a 5-hour plane trip that requires a certain amount of planning. Personally, I don’t think the distance between Chicago and Minneapolis is insurmountable.

    That said, you’ve been talking long enough that it’s time to make plans to meet in person. It’s also worth discussing early on whether or not either of you would be willing or able to move if it came to that. Many people with kids, or even certain types of jobs, don’t have that mobility. I also doubt that a guy who is having lengthy phone conversations with you over a period of weeks is a player. Players generally don’t want to put that kind of time in a relationship over such a distance. You don’t want to let expectations build up to such a degree that when you do meet, if it doesn’t work out one or both of you is terribly hurt and disappointed.

    There is one thing I’d like to make crystal clear: many marriages are a sign of how CONVENTIONAL the couple is, not how committed. They marry because it’s what’s expected of them or because they think it’s “time.” If they were really so committed, would the divorce rate be as high as it is? That’s not to say that some unmarried older men simply don’t want to get married. If you’ve had such lengthy phone conversations, has the subject of relationships ever come up? Has he ever lived with anyone? Been in a long-term relationship? Don’t interrogate the guy, but don’t be afraid to ask tough questions because you’re afraid of what the answer might be.

    That’s the problem with many dating rules, they don’t take into account that every person is different, and has had a different experience. Rules are great as guidelines, but let your own experience, knowledge, and gut feeling, be your guide.

  8. 8

    GREAT post. I concur!!!

  9. 9

    @Ava #7

    “There is one thing I’d like to make crystal clear: many marriages are a sign of how CONVENTIONAL the couple is, not how committed. They marry because it’s what’s expected of them or because they think it’s time. If they were really so committed, would the divorce rate be as high as it is?”

    Clap! Clap! Clap!

  10. 10

    Being 42 and single, and having never married is not a red flag; at least not for me. Potential red flags come up after I know their history, as there can be reasonable and understandable explanations for their current status. I do not believe he is a player either, based on your experiences thus far. I think the biggest issue is the LTR situation.

    I hear from loads of men who live in different states from me, yet I will not engage them in anything long distance. I know what my boundaries are and I know that I will not and cannot relocate for someone at this time in my life nor date with any regularity, if he’s a thousand miles away or even a hundred which can also be difficult. And honestly, I am always a little perplexed by the guys who continue to state that distance is not a problem for them, unless they are a traveler likely looking for an out-of-town fling. They could even be married.

    But this is not about me. If you feel that strong of a chemistry and connection with him, then try to meet as quickly as you can vs. continuing to put the cart before the horse. While the odds are not great for successful, long-lasting LTRs, they CAN work, so all the best to you.

  11. 11

    Can you imagine anyone, dating expert or not, advising people not to date divorcees in their 40s?
    I do.

    I advice people who have never been married to stay away from divorcees. In fact, some Jew said a really long time ago that it is adultery to marry a divorced person, or for a divorced person to remarry.

    I would rather marry someone who is 21 and had never been married, even though I would not have much in common with her, than I would marry a divorcee of any age.
    Maybe he didn’t want to take a vow to be with someone the rest of his life if he was unsure in his heart that he could keep that vow. Unlike his counterparts who took such a vow, believing they could always get a divorce if the marriage became untenable for whatever reason.

    Perhaps, just perhaps he might be a more sincere and loyal partner than someone who married to go along with his partner’s wishes, or some other spurious reason. One thing we know, a marriage license is no guarantee someone won’t cheat.

    Seems to me, the only way to determine if a 40-something, never-married, person would make a good partner would be to get to know him/her IN PERSON. Then decide.
    Great advice.

  12. 12

    I think if a 42 year old man I was interesting in told me he had never been married, I would be listening with a raised brow. I wouldn’t write him off completely, but…

    One thing I have learned the hard way is to really, really listen to what he tells you, no matter how significant it may seem, including jokes, stories of other people, you name it, because there are clues there, big ones. If you let someone talk long enough, they will tell you everything you need to know.

    searchingwithin´s last blog post…How Will We Love?

    1. 12.1

      That’s so true and its also wise to not let youself get too attached too soon so you’re able to really take it all in and not focus in on the whole picture. I think its really hard when people are older because they are having to sort through people who don’t want commitment or people who’ve been burned in a marriage that failed. Most of the long time bachelors I’ve seen around or I hear abour well they seem to stay that way. If I were single I would be leery of them if I wanted marriage or something long lasting. I think they mainly prefer friends with benefits   or to be alone most of the time. I think people that need someone get that if not they don’t.

  13. 13

    In these long talks why not ask him about his past relationships?

    1. 13.1

      I’m 43 and have had none.   Once a woman hears that there’s no chance for me.

  14. 14

    Can’t we perhaps flip this and say that Kate is actually expanding her options and her chance to find love by considering someone who is outside her local area?

    Also, some divorced men I’ve met have had crippling baggage. They may even want to re-marry, but that doesn’t necessarily make them great prospects. The divorce rate for second marriages is even higher, something like 70%, I believe.

  15. 15

    Well, this is a topic I can relate to. First of all…Steve, guy you definitely spoke words of wisdom and truth,standing O. Searchingwithin, you also shed some great light on this as well. Michael? are you refering to Jesus? the “jew”? If you are a believer maybe you should refer to Him with His name. Some people may or may not believe as you or I do. With respect….
    What I do know is that I too, actually tried not to get involved with people that had never been married only from the standpoint that the experience of actually making that commitment hadn’t been made in the past. When we marry things do change…some for the better some for the worse. We learn, I know I have, alot about being married. So, with that being said listening to the above comments and Evan…my viewpoint has changed. Just like I wouldn’t want anyone saying they wouldn’t want to get involved with me because I have been divorced twice. No one knows the actual events that led up to both of my divorces. Domestic violence and well a red flag “I should” have paid attention to in the beginning of the last relationship. There you have it….you NEVER know what the circumstances are. I don’t want anyone ever assuming things about me, so…why should I assume about them. Like Searchingwithin said, after many conversations….you will eventually find out what you need to know, but you have to PAY ATTENTION. Don’t start out or leave the rose colored glasses on….take them off and see, hear, and feel what is REAL. Lots of stories out there…many different stories with nothing cookie cutter about them. Investigage everything! My thought process was there for my own protection….fear of being hurt. Trying to find the safest best bet I can. Can I really? No. No pain, no gain as the bodybuilders like to say…feel the fear and do it anyway….what doesn’t kill you only makes you
    stronger…and on and on……that is how we learn and grow….so here I go, learning and growing! Hang in there Kate, just be aware of the red flags….pay attention to them, they are REAL!

  16. 16

    I agree with the sentiments that other’s have expressed about keeping your eyes open to red flags in general and would like to take it a step further- in all of my relationships/dating adventures, there were signs as soon as three months in, even more quickly in most cases, of potential problems or red flags. Sometimes it was just a gut feeling, but it was a warning nonetheless. I chose to ignore them and that’s where the problem comes in. It’s not that liars and bad people are so adept at hiding who they really are- i propose it’s that we refuse to listen/pay attention/take appropriate action most of the time.

    I think we can all save ourselves so much time, heartache and trouble if we learn to heed these flags instead of talking ourselves out of them or hoping/waiting for things to change. If we trusted and believed in our ability to know pretty early on whether someone was shady or not, we’d be less worried about trusting people in general, which would only help our future relationships as well.

    If we start picking up on these warning signs early on and taking appropriate action (usually leaving), we’d decrease our chances of being 42 and never married (if married is what we want to be) or 42 with multiple divorces and/or deep scars and emotional baggage under our belts.

    And for those that are already in that boat, learning from past experiences and *behaving differently in the future* is the most important thing. It’s never too late.

    1. 16.1

      its all bs they all are player in my book I don’t date no more because of that.

  17. 17

    I have to wonder also, if they talk often, for as long as 5 hours at a time wouldn’t some information regarding previous relationships naturally have come out? I know some people are more private than others, but still…when you get to talking about the things you’ve done, the places you’ve lived, details of your life are revealed even without direct questions.

  18. 18

    Great post as usual Evan.

    Personally I would not date a guy over 40 who hasn’t been married, that is a long time not to legally commit… not even a youthful, silly marriage? Major Red Flags, imho.

    This time last year I ended it with a 43 year old never married man, found out he was a passive-aggressive player, by listening to what he said about the women in his past.

    The only woman that he lived with (for three “crazy” years), she was the one who proposed to him and he was reluctant to marry and never did.

    What all his failed relationships had in common was HIM.

    Lesson learned. Now dating a man who has been previously married and had several long-term relationships…

    1. 18.1

      “What all his failed relationships had in common was HIM.”

      So this guy would’ve been a better choice if he had been previously married?

      And if they were marriages that ended in divorce (which they would’ve HAD to be, for him to date you), what they would all have in common would still be HIM!

    2. 18.2

      I’m even lower than him.

    3. 18.3

      I do think that alot of these dyed in the wool bachelors   may have personality disorders that make it impossible to sustain relationships and they break alot of hearts when women try to make something happen with them. I’ve seen it up close and personal and it gets to be pretty predictable. I dont blame someone for wondering what they’re in for. If I were single I think If. I were single I would probably pass . Let some other gal take that challenge.

      1. 18.3.1

        Imagine YOU being single and into your 40s, and  never married simply because of circumstances in your life, and being told you are defective in your personality, feels good huh?

    4. 18.4

      That’s terrible reasoning.     Someone making a poor decision (“youthful, silly marriage”) is a better choice than someone who wisely chose to skip that mistake?   Women who think that way are doing the guys a favor as they apparently have little respect for marriage and see it more as a rite of passage than what it should be — a one-time, life-long commitment.  

    5. 18.5

      Typical American Female.   honestly, this is one of the main reasons why ANY guy over 40 should look long and hard to overseas relationships.   No matter what a guy does, he will never be good enough in any American womans eyes.   I like the biggest key word of your post….(Now dating a man…..) Yeah, women here in America want a guy who is broken in and beaten down and battered up so he will bow to her every beck and call.   You pretty much some it up that your also a player and as funny as it seems, still NOT married.     In closing here is the facts of American women: You women all complain about the guy being a player, then you complain if the guy has baggage, then you complain if the guy is over 40 and never married, then you complain if the guy wants to go out with friends for a few hours, then you complain if a guy is still a virgin in his adulthood because he wanted to wait for the right time, then you complain if a guy sleeps around with every woman under the sun.   Moral of the story is this, you will never be happy with anything we do as men.   So my suggestion is why don’t all of you just go out and become nuns?

    6. 18.6

      What about a 43 year old virgin?

    7. 18.7
      Elizabeth Rochelle Dickson

      I think it’s   silly and immature   to insist   on having been married   or in a long term relationship   before   as an automatic   “no” for a man over 40. He may well take commitment   seriously   enough   that he just won’t   do it until he’s   ready to be serious. I think more people   ought to stop rushing   into relationships   to fit conventional   “wisdom”. I once accepted a marriage   proposal   because   I thought I was supposed   to, even though   I   couldn’t   be   less interested   in marriage   at the time (I’m   still firmly   in   the   “nope” category at 42! I’m   female, and nothing sounds less appealing   than being married; I have never looked at a wedding   dress with more   thsn mild interest, and have never, ever planned “my perfect   wedding” more than   “meh, black   lace dress (I happen to like them and own 3.) at the courthouse… whatever.” ) if he had paid me. Turns out my reservations   were well founded, as he was an ass and a liar. But seriously, some people   just don’t   really   care for long term relationships   OR marriage, and find it super irritating   to be thrust into some kind of armchair   pop psychological   box of “something is wrong   with   you!” Dude, maybe something   is wrong with YOU for pushing   your insecurity   on us.

    8. 18.8
      broken-hearted girl

      Almost 2 months ago I ended a 2.5 years of a relationship with a never married man at 42. He was successful, extremely well educated and cultured and was promising a future or a marriage together btw I am currently 34. We were getting ready for a marriage and we even had the papers ready. He was very serious on getting married from the moment we met. He was talking and planning a life with me in it.I would never think of the age over 40 that never married before would be so difficult to date. Please offense to anyone who hasn’t met their significant other yet this is not for you of course but pay attention to some of the things why this is not working out. The way I ended the relationship wasn’t mature at all but let me share my side of story a man on his early 40s were waiting for his retired parents to come to my parents for almost over 6 months.They were living in another city but a 42 year old man was really so stubborn- so difficult to be convinced that it was time we organized the city hall and stuff until his retired parents who literally have plenty of time to make it to my city. This 42 year old man was as stubborn as a donkey was that he didnt prioritize us to organize the very simple wedding ceremony and was still asking for his mom’s approval on anything that I was trying to plan.

      I asked him actually I literally threatened him that he eithers ask his parents to come and meet mines asap or I leave. Because he was always coming up with some excuses that his parents have this and that and they will come eventually but he doesnt know when and he can’t even ask them an exact date or convince them or organize the date.

      sorry if this sounds too dramatical to you but I really had been patiently waiting for a yearfor this to happen but he never paid attention to what I wanted to do how I wanted to feel he was always nice to me and such and I loved him a lot that I had to accept most of the negative things that he carried too.

      What I am trying to tell here is it is really almost impossible for someone to convince a stubborn 42 year old man to do sth out of his wish. he was very open with me why the previous relationships didn’t work. All I can relate was that he wasn’t accommodating. I was the one who was accommodating the most time. It was his way or the highway. It was only his family rules not ours. It was always his ground rules in the relationship he did not care about his gf feelings.

      A man who has never married before and was making his way towards a marriage with me, planning a life with me, gathering the docs (by my force) made me realize If I was to marry this man it was always going to be his way. If I wanted a different way it was impossible. and that made me realize his age and marital status had made it so clear that he had no tolerance towards making a relationship work. I think it gets even harder to date after certain age. you have your own rules and truth and not flexible to come to a mutal way with your SO!

      There are solid mistakes that I have done in this relationship too I was always walking out of on him after our fights because he was CONSTANTLY shutting down and STONEWALLING whenever I came up with a problem talking to him.

      I still cry every day and it is really difficult to digest this break up even tho I ended it myself. He didnt want to try tp make it work because he had golden rules of if anyone was leaving the relationship he wouldnt stop them.And it was a red flag.

      We all have problems we all have crazy side negative sides. what I believe is that now certain age and certain types are single because they never want to change.

      Thanks for reading my drama-filled post. Thanks for all your coming up comments. Positive and negative ones are all welcomed. Stay hungry stay foolish!

  19. 19

    Breaking it down as you did was great. As to the question she asked though I don’t think it’s a red flag on it’s own that he is unmarried and 42. It’s possible he had been quite busy with work when he was younger or had family commitments keeping him from the dating scene. He is talking for 5 hours at a time which is positive but you should honestly look out for yourself. It’s possible that this could work out but as Evan already pointed out the odds are against it.

  20. 20

    To searchingwithin #12: That is a very good point about listening. I have noticed that being a truly good listener takes skill, patience and tolerance. I try my best to not interrupt people or focus on what I am going to say next rather than focusing my direct attention to what they’re sharing. Most of us just want to be heard. 🙂

    I remember reading an article a few years ago about men and women in their 40’s and 50’s who had never married finding love through a dating site I believe. Most of them had been highly focused on their career. And I personally know some great men in their late 30’s, early 40s who have also not married due to their careers. I think a red flag for me would be when they have had no long-term relationship experience. Being single and independent for so long can make you pretty self-serving and set in your ways.

    Another consideration is what the writer is looking for. Is she hoping for marriage someday, etc.? It may turn out that he’s just fine, but doesn’t believe in the institution of marriage, and if that’s what she wants most, they won’t be a good match any way.

    WithLove #15 is right, too, about making assumptions. One never knows why someone divorced or did anything in their life until they know their story. It is very possible to exit a divorce as a much more knowledgeable, evolved, and finely-tuned human being. Adversity only makes you stronger and wiser.

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      I think about not having any long term relationships is pretty telling. But really its all scary because I’ve met some pretty weird bachelors and their stories are varied but the basic theme ofhow they run their life tends to be simular and the older they get it seems the more they just stay on their own. They are usually really into their friends and maybe parents and siblings and that’s it. They’re usually very picky whether they’re good-looking or not. They’re veey really skin averse and feel less stress being   single without so much responsibility. I don’t know of anyone who has suceeded with a guy like this.

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        I meant to say risk averse. In other words they worry alot about what could go wrong or who they might miss out on. Its funny too because wether they are successful they act like they are such a catch and are kinda arrogant. One of my friends was dating one and over time he began to really boast that he could have almost any woman he wanted and the guy was so not cute! Very he was a legend in his mind.

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