Advice - haggard

Dear Ian:
I am a 33 year old gay man who recently begun dating a 23 year old guy. We have been on three dates so far, and things are going great. He tells me that I'm really sweet and that he really likes me. I feel the same way about him. My problem though is that I have been in this situation with different guys (almost always considerably younger than I am by the way) tons of times over the years. Things never work out for more than a couple months. I can't help but assume that things will end up the same way this time, even though I'm very happy now. How do I deal with being old and jaded while he is young and optimistic?

Dear No Name,
Your age difference is reasonable. More than a decade and you're pushing it, under five years and I don't think you should consider it worthy of mention. But people are probably going to notice right? You're going to naturally look more haggard than him and, when it comes down to it, you were raised in different realities. For you coming out in high school was just not done-- 1993? He may have been out since high school. Happily out in High School if I believe my siblings who seem to have out gay friends and are still juveniles.
You mention that you've been in the same situation "tons of times" over the years but they never work out for more than a couple months. The common factor in that story is you. Is he meeting you in the middle and being more mature for your sake, or are you acting like a 23 year old and that's why you keep dating younger men? Could you see yourself with a 43 year old man? Because in order for this to last he needs to see himself with one--you in ten years.
A relationship with an age difference is still a relationship. If you focus on the age difference as an issue then it will be an issue. If when you mention dating younger men you mean they are always ten years younger, then fine eventually a ten year difference will work out. But if this a trend--as in at twenty-five you dated twenty-three at twenty-nine you dated twenty-three at thirty-one you dated twenty-three. Then eventually you're going to need to mature past twenty-three, or start shelling out cash for some hos. Even if you don't think you're doing it, you might not looking for a younger model but looking for a fresh start. Did you come out at around 20-23? Are you focused on that age because of it? Maybe. Just sayin'.
Of course this leaves the guy out of it, ignores my straight readership and is waaay too cynical. Just return the favour, when he expresses his love express it back. Take the days at face value, and double check--are you with younger guys because that's your taste, or is it fate that brought you together and one happens to be younger? Keep stock that I'm 8 years younger than my boyfriend and I think he's the bees knees...age difference is only the problem if you think it is.

I am always looking for more letters seeking advice. Your identity will not be revealed and I promise I'll reply to every single letter on the blog. At this point I'm not famous enough to worry there will ever be too many. Maybe you're a straight woman, a straight man? They seem to be under-represented so far. Email me at Ian_Mullan@hotmail.com.
Also, I'm going to be doing a financial advice column soon with the help of the blog's financial market researcher Terry Parsons (interviewed in the September 24th edition of the blog) so send in your money problems and we'll try to help. Ian_Mullan@hotmail.com -- any advice you need? I gots.