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Thus, if you have preconceived notions about gorgeous people, rich people, short people, gay people, Irish people, etc – those notions probably came from SOMEWHERE.
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? 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?
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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Just over three years ago a long dry spell in my dating life ended when two women asked me out on the same day. During that time I also started reading dating advice, so now I have a better understanding of what I’m doing. It’s unfair to make a judgement call on this guy based on superficial characteristics, but Evan echoed my sentiments. Can you imagine anyone, dating expert or not, advising people not to date divorcees in their 40s? Instead, dating experts will advise people to date that demographic, but be alert for warning signs. I’m cynical about the prospects for long distance relationships so I would advise you on *that* factor alone to move on. 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.
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. I hear from loads of men who live in different states from me, yet I will not engage them in anything long distance.


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. 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. 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. 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. 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? 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. And for those that are already in that boat, learning from past experiences and *behaving differently in the future* is the most important thing. 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?
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? 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. 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! 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. The unhealthy part of stereotyping is not necessarily the stereotype itself, but the assumption that ALL people in the category fit the stereotype.
Unlike his counterparts who took such a vow, believing they could always get a divorce if the marriage became untenable for whatever reason.
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? 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. 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. 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. Rules are great as guidelines, but let your own experience, knowledge, and gut feeling, be your guide.


Potential red flags come up after I know their history, as there can be reasonable and understandable explanations for their current status. 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.
If you feel that strong of a chemistry and connection with him, then try to meet as quickly as you can vs.
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. They may even want to re-marry, but that doesn’t necessarily make them great prospects. 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.
We have great long conversations, many that last 5 hours long, he’s commented how great our conversations are. 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.
Personally, I don’t think the distance between Chicago and Minneapolis is insurmountable. 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.
Most of the long time bachelors I’ve seen around or I hear abour well they seem to stay that way. What if he spent five years in a dead-end relationship and has had difficulty getting back out there? If a man assumes the same attitude, how is that wrong while the woman is admired for being empowered and independent? I also doubt that a guy who is having lengthy phone conversations with you over a period of weeks is a player.
If you’ve had such lengthy phone conversations, has the subject of relationships ever come up? While the odds are not great for successful, long-lasting LTRs, they CAN work, so all the best to you. Players generally don’t want to put that kind of time in a relationship over such a distance.



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