Email from a guy with a potential boyfriend situation

A week or two ago, I was happy to get an email from the South African reader who'd had a problem situation with his ex-boyfriend. The email was as follows:

Dear GB,

I know I have written one of these letters before, and that it might seem impertinent of me to do so repeatedly, but I am again in some personal distress. Your prior advice certainly was helpful and I was hoping that you might have some of the same for my current situation. I usually take ages to reach a decision of any importance, and to do so I try to accumulate as much information as possible. How else is my decision supposed to be informed?

Things have worked out quite well since I last wrote. I have actually been out and about so much these last few months that I hardly ever have time to worry about my silly ex-boyfriend situation. Ah to be young, stupid and insecure!...

I still pretty much believe the Internet is a bust (I am sorry guys, but it is true, for me at least) I still mostly get horny 18 year olds or hornier 50+ year olds replying to my ad(s). [Yes, I created multiple profiles for all the different interesting sides of my person - no one has seemed to notice... ] I really am not into copious quantities of casual encounters, so I end up meeting a few guys who sound nice but who actually still feel slighted that I turn down their offers to go home with them after dinner. They tend to just not reply to my messages after that. I consider that rude, and my profiles have all been swept from the information highway!

I have actually reconnected quite well with four or five of my (our) old friends. It turns out that attending parties with them and my ex is not even half as bad as I expected. Dragonzlad was spot-on in his prediction. I get more attention than my ex does anyway ;-) These old friends live about 100km away though, so I only see them about once or twice a month.

The fun part has actually been smiling at men, that does work! Thanks Kevin. I also made a new friend through the woman I share a house with, he introduced me to his friends and voila; instant support structure if you please. I went out with them a few times, got to know the hangouts and after that I even became confident enough to go out alone. I am friendly with everyone who comes up and talks to me, and have had the most stimulating conversations. Before I knew it, I had invitations and phone numbers (and even some casual encounters with amazingly hot men). People were warming up to me because I warmed up to them, as Monty implied they would.

I took Dreamer's advice and accepted each invitation I got, some truly were uncomfortable and unfun, but most dates were enjoyable at least. I think I might even have met people who will turn out to be long term friends of mine.

And now I have finally met someone I feel a connection with, someone with whom I feel I can have more than the all too common one-nighter. We have been 'dating' now for about six weeks, casually you understand. One or two nights a week we go out for dinner or stay in with a movie. We get along swimmingly during these evenings which invariably end in me staying the night at his place. I have fallen for this man, and I would like the affair to graduate to relationship, the next logical step. How to breach the subject though?

First a little more background: He is about 20 years my senior (in his forties), I have no problem with that, but he has said that it is something he is uncomfortable with. As a fairly long term bachelor and traveling a lot, he is very used to his way of life. I expect that he is used to his affairs being casual though I haven't asked him about that candidly. I am also fairly certain that he is currently seeing other men as well, another fact that doesn't bother me half as much as I thought it would in the past. I haven't questioned him about this either. Up to now we have been having fun together, and I was not expecting exclusivity or gestures of commitment. I have been dating other men too, but none of them have piqued my interest as this one has.

Some time during our last date, he confessed to me that in some time he hasn't felt about anyone as he feels about me and that he had no idea what to do about that. He even informed me that I have the approval of his friends (not that I think he should need their approval). Since then I have started to hope for my fairy-tale ending and it is driving me insane. Do I or do I not start up a conversation about a relationship? If I do and he does not feel as serious about me as I infer he does, it might be the end of it all, no more fun for me (not that I think I will be able to continue as casually as before after confessing to myself that feelings have developed).

What was I thinking? As if life is not difficult enough without me falling for the one person whose feelings I cannot read with any accuracy! My friends (who have not met him) are of different minds: some think he is just unsure about me and my intentions, some that he is unsure about himself his own intentions and some are certain that he is playing me. These friends of mine have no experience with men of an age with him, so I do not trust their judgement implicitly in this matter. Maybe you or your readers have some insights into the mind of an older man...

Thanks for all for the excellent advice last time, and thanks GB for initiating your agony Uncle (or would you prefer Auntie) postings!

Yours sincerely, as always,

Looking through this reader's new email, I'm glad that the advice we all gave proved so useful. So I guess it's no wonder that he's written to me again, now that things have progressed to the next stage :-).

It's interesting that he finds himself attracted to an older guy. One of the attractions of older guys can be their confidence, because by the time a guy reaches his forties he's likely to know his place in the world, and hence have lost all his insecurities. The good thing is, if a guy like that commits to a relationship, he's not likely to change his mind for any trivial reasons.

The good thing is that it's clear that the older guy is starting to think the same way as the reader is. Why else would he have mentioned the fact that his friends approve? But I disagree with the reader when he queries the importance of the approval of the older guy's friends. In any relationship, both guys are likely to have friends from before they met, and it's important on both sides to keep those friendships going. Friends are important to fall back on in case the relationship ever fails. Also, if a guy can't get on with his boyfriend's friends, I think it increases the likelihood that the relationship won't work out long term.

Rather than discussing relationships, I think the next step should be for the older guy to meet the reader's friends. He said that they have not met him yet, and I think they should. They'll be able to give the reader a much more informed view about his potential boyfriend once they have met him. And if for whatever reason the older guy doesn't get on with the reader's friends, that'll give the reader something important to think about. It would certainly be best to know about that in advance.

I reckon small steps are best to try and find the fairy-tale ending that the reader's hoping for. Only once every piece is in place is it worth talking more seriously about relationships, and it sounds to me as though that point hasn't quite been reached yet.

I also doubt that anyone can really read a potential partner with any certainty. If one could, there would be no mystery or excitement in the relationship, so I doubt it would last. And lastly, I'm not the kind of gay guy who feels particularly comfortable in a woman's clothes, so I'd rather be an Uncle than an Auntie LOL!

Do any other readers have any thoughts on this subject?