Rules for dating after 45???

[Hepburn]

OK, I am having this discussion with a single guy I know. He is in his early 60's and I am not far behind. We are friends and have more of a business relationship than a social one. But, apparently he values my opinion so he asked me some questions about dating and what I expected in a guy who dates me. And, btw, I don't think he is hitting on me. Just wanted my opinion. So I am looking for some opinions from people who are (please forgive the expression) older. One thing about this guy is that he has never been married and never wanted to get married. So this may be an important factor and he tends to date women in his own age group - maybe 7 or 8 years younger at the most. He is accomplished, has pretty good manners and is decent looking, makes a lot of money and from what I can gather, usually takes his dates to some pretty nice places. He just cannot seem to keep a current girlfriend, but does seem to keep some former girlfriends, maybe about 5 or 6 of them, as old friends and still sees them - but nothing romantic according to him. Sees each maybe once every other month at the most.

IMO: From what he has told me, I think he has a very off idea of what a dating relationship is and it does not figure with what I think at my advanced single age. (BTW: I have been widowed for a long time. So I think he asked me because I don't seem to have a sour attitude on men and most of my friends are guys and even at my advanced age, I have a lot of dates and most are with guys that are really good friends more than anything else.)

It's like he compartmentalizes women - they are either dates, dates he is sleeping with, female friends or female friends he is sleeping with. I think this is his problem. He is looking for someone "nice" to date - maybe not exclusively - but to go out with when they are available. I asked him why he wanted some sort of steady date and his reply was, "I want someone who makes me feel good." Odd response, IMO.

I have met a few of his past dates because of business reasons and I did not say this to him, but IMO they are not real impressive. Not interested in anything political or aware of any current events, do not understand many things, seem rather dependent and while I worked with them on business matters, the nicest thing I could say about them is that they were really not offensive - but none seemed to have any personality or awareness. Just kind of nothing. The kind, too, IMO if I said to go sit in the corner for 5 minutes while I work they would do so without question. Not exactly Stepford Wife material, but real close.

So.....I am thinking about telling him that he is looking with all the wrong reasons and all the wrong ways to get a steady date. IMO: No one, male or female, at an older stage of life wants to date someone on a steady but uninvolved basis - that's probably true of younger people,too. He seems to not understand that part of a dating relationship leads to becoming good friends and not dating. Most of these women are looking for someone not just to date on a Saturday night, but someone who is a friend and who they can pal around with. I can recall one conversation that he had with one of his girlfriends in front of me that was a real eye opener: She asked about what they where doing on an upcoming Friday or Saturday evening and he plainly said to her that he had a date with someone else. She said that she understood that they were dating and his reply was, in essence, that he just preferred to be with someone else on that evening and not her. She started to cry, left and I think he has not heard from her since. Now the problem is that he cannot understand why this may not have been the right thing to do. He was not mean about it, just a bit too factual IMO without consideration for the other person's feelings.

Is there any hope for this guy? What the heck would you tell him and I am asking seriously. I think he is broken and cannot be fixed, but maybe there is something I can say that will give him a clue on why his steady dating just does not seem to work out.

How about some really good rules from you successful daters that I can use? I tried telling him that I thought that people of both sexes in our age group were looking for a good friend first and that the dating thing on Saturday and restricted times was not very appealing and that was part of his problem. But I just do not know how to clue him about not saying something like he did to that one girlfriend about he would rather be with someone else. He is basically a nice guy,albeit clueless, I would not date him cuz he and I are so politically opposite that every conversation would turn into an argument!

Thanks for any help you can offer and sorry this post is so long...but I am just kind of clueless about what to say to him.

[chiburb]

1. I'll let others respond more thoughtfully, but...

Regarding this:

"She said that she understood that they were dating and his reply was, in essence, that he just preferred to be with someone else on that evening and not her. She started to cry, left and I think he has not heard from her since. Now the problem is that he cannot understand why this may not have been the right thing to do. He was not mean about it, just a bit too factual IMO without consideration for the other person's feelings."

If a guy in his 60's can't be honest, then what's the point? He was blunt, but honest. Isn't that better than leading her on? He wasn't closing any doors to her, just for that one night. I think her (and your) reaction was over the top, not his.

Gee... an honest man and that's not good enough.

(Gotta go, I'll check in for the flames when I get home.)

[notadmblnd]

10. Sounds like he does not wan't a relationship with a woman

but he's dating women that want relationships. Cheap meaningless sex has it's merits too but he should be upfront to begin with and date women who share the same value. There are women out there that have done the marriage thing and don't want to do it again. Those are the women he should be going out with.

[hedda_foil]

2. If he's reached this advanced age ...

If he's reached this advanced age and still thinks as he does, he's not just clueless, he's hopeless. The man doesn't want what any worthwhile woman would consider a real relationship. In fact, he doesn't even want what any woman at all would consider a relationship. He's too old to change and no doubt he doesn't feel any particular need to do so.

[supernova]

4. I agree with this

In fact, he should make it clear to future "dates" that he's just interested in platonic friendship, an occasional outing -- nothing more.

That's also the reason, btw, that he keeps attracting people high on the so-so meter. Anyone who's interested in having a serious relationship is passing him over because they see he's not emotionally available.

How's that for third-hand pop psychology. :-)

[Hepburn]

7. IMO: That is what I am seeing, too.

Yep, and the so-so material says it all. He is not looking IMO for quality but a situation in which he will always have the upper hand.

Wow, how sad to go through life and be so clueless.

I just did not know what to say to him...so I am thinking that it would not really matter at all maybe cuz he would not understand.

[ihaveaquestion]

3. Sounds like he lacks empathy for others or

the ability to imagine how his actions / statements affect others. Typical narcissist and there is probably no hope for him without therapy.

Just my quick take on it.

[Hepburn]

5. Thanks for the opinions....

...and so far you guys are pretty much confirming what I was thinking about this. I just do not know what to tell him - since he asked me for some pointers - and I am thinking that just saying something like, "well, just keep trying...maybe you will find someone who you are compatible with!"

Yeah, IMO, he does lack a ton of empathy. It is not like he is mean on purpose - he just does not understand.

[trof]

9. Sadly a lot of us guys still don't "get it".

And I just realized I could have a nifty double entendre going here, but I don't mean to.
;-)
If I can blow my own horn a little, I think I'm more tuned in and empathetic because I was raised by a single mom. IMHO, it made me a better man. Miz t. thinks so, anyway.
:-)

[Demobrat]

6. OK. What he wants in a dating relationship

is somebody to make him feel good. If you asked him what he expected to give in return, he sounds like the type who would not understand the question. Therefore, it appears to me that what he needs is the number of a good escort service.

[TexasBushwhacker]

8. Clueless - you bet!

Well, since he is dead set against marriage, for whatever reason, he needs to be clear about that up front. To me, the easiest way to do this is through personal ads or online dating like Match.com. You get your "dealbreakers" out there, up front. Anyone that shows interest in you knows what your issues are. He may very well find an older lady who is financially successful in her own right and is not interested in a marriage type commitment. There are women out there who don't want to think about having to share and share alike just like there are men.

His "method" of dating with complete and total honesty about who else he's dating is going to work great until he meets a woman just like him who is dating someone else. At his age, most people like the idea of finding that certain someone to grow old with. They like that security. Unless he has money, in which he'll always find someone who will date him with any conditions he chooses, he will be a lonely old man and will die alone. Most people don't want that. If he does, that's fine, but he should know what's around the corner.

[KG]

11. dating after 45? there's such a thing?

do tell!