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Older guys
#1
Hey,

I'm 30 years old and have been out only recently. I'm very attracted to older guys, 50+ and want some advice on safe ways to meet older guys for hookups or may be more. I've come close to trying to meet someone on craigslist, but I have no clue if its safe or not so I have not gone through with it.

I just moved to Chicago so if anyone knows any specific places that's be cool also.

Thanks
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#2
26 year old guy here with a 60 year old partner. Intensely attracted to him, if I wasn't with him I'd be with someone a few years older or younger so, yeah, I get the attraction to 50+

Older or not, safety is safety. Follow all of the usual rules. Don't meet someone for the first time in private, ever. Ever. E V E R. Ever. Always meet in a public, well populated place. Mall, coffee house, restaurant, book store, whatever. Tell him you'll be there at X time, but never actually GET there then. Always be 10-15 minutes early. Why? So they won't see who dropped you off or the car you drive. Don't let them see the car you drive, so they can't get a license plate number and stalk you. Think I'm kidding? Google stalkers. The internet brings every sick bastard to the table. Take every single precaution in the world if you don't know somebody.

Some members will probably disagree with me and just say wing it. Do hookups, meet them at your apartment/house or their apartment/house and get busy. Me? I think that's a tremendous way to get yourself into an ass load of trouble. Do some of the above things like I mentioned (public place, well populated, arrive as secretly as you can) and get a feel for the guy. My advice? Do this a few times before you consider "hooking up" I know that kind of goes against the rules of "hook ups" where it's supposed to be mostly easy, anonymous, or in-the-moment, but it's your life. The fact that you're questioning safety tells me that you at least want to go about meeting guys in some form of a safe way.

I'm not wired for hookups, just relationships. I can't have sex without a relationship. That's just me though so I'm not judging you, just saying I can't help with the how-to-do-hookups thing. I CAN tell you about staying safe though, considering I met my partner online. But I did some rather unsafe things in meeting up (though everything obviously worked out) but I know of what you should/shouldn't do.

Probably best advice is trust your instinct. If something is telling you this dude doesn't feel right/somethings off, just leave. If you feel okay with him, keep talking and meeting up. Just take things slowly, even if you just want sex. Better safe than sorry. Other people here will probably disagree with me but oh well, my opinion and all that.

Oh, and condoms. CONDOMS!!!!
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#3
Hotel bars, I've found, are excellent for meeting older men.

And everything [MENTION=22914]Cobalt[/MENTION] already said.... x2.
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#4
This is purely anecdotal experience, so take my words with a grain of salt, but I've found that bazaars, museums and antique store are excellent places to meet older men. I totally get the attraction to silver foxes, and I've found my share in those sorts of locations.
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#5
omfg .. i thought i was the only one .. love older guys too .. heehee ..
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#6
Most major cities have a gay bar for every flavor... drag, twink, leather, dance, pool, lesbian, strippers, and what I lovingly refer to as a "fern bar" ... where older guys congregate to talk and drink. If you're in Chicago, I'd wager that there are a ton of fern bars around. They're more than likely in older, historic parts of town in little out of the way, hole in the wall type settings.
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#7
Cobalt Wrote:26 year old guy here with a 60 year old partner. Intensely attracted to him, if I wasn't with him I'd be with someone a few years older or younger so, yeah, I get the attraction to 50+

Older or not, safety is safety. Follow all of the usual rules. Don't meet someone for the first time in private, ever. Ever. E V E R. Ever. Always meet in a public, well populated place. Mall, coffee house, restaurant, book store, whatever. Tell him you'll be there at X time, but never actually GET there then. Always be 10-15 minutes early. Why? So they won't see who dropped you off or the car you drive. Don't let them see the car you drive, so they can't get a license plate number and stalk you. Think I'm kidding? Google stalkers. The internet brings every sick bastard to the table. Take every single precaution in the world if you don't know somebody.

Some members will probably disagree with me and just say wing it. Do hookups, meet them at your apartment/house or their apartment/house and get busy. Me? I think that's a tremendous way to get yourself into an ass load of trouble. Do some of the above things like I mentioned (public place, well populated, arrive as secretly as you can) and get a feel for the guy. My advice? Do this a few times before you consider "hooking up" I know that kind of goes against the rules of "hook ups" where it's supposed to be mostly easy, anonymous, or in-the-moment, but it's your life. The fact that you're questioning safety tells me that you at least want to go about meeting guys in some form of a safe way.

I'm not wired for hookups, just relationships. I can't have sex without a relationship. That's just me though so I'm not judging you, just saying I can't help with the how-to-do-hookups thing. I CAN tell you about staying safe though, considering I met my partner online. But I did some rather unsafe things in meeting up (though everything obviously worked out) but I know of what you should/shouldn't do.

Probably best advice is trust your instinct. If something is telling you this dude doesn't feel right/somethings off, just leave. If you feel okay with him, keep talking and meeting up. Just take things slowly, even if you just want sex. Better safe than sorry. Other people here will probably disagree with me but oh well, my opinion and all that.

Oh, and condoms. CONDOMS!!!!

That is sound advice. Even in a rural setting where everyone knows everyone...you just never know about people.
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#8
I have heard that in urban areas, craigslist tends to attract a lower quality guy than using apps, so it's possible that CL is not the right tool for you in Chicago. There is probably a big segment of the older population that doesn't use apps but would be open to meeting in public. Chicago does have bathhouses and one is more known to attract older guys.

I always heard the term "wrinkle bar," or "piano bar" as places where "older" (30+ lol) guys tend to congregate. Meeting guys in real life should not be at all hard in Chicago, just be the one to say hi first. A lot of older guys will have no idea you are into them unless you make the first move.
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#9
Going on 9 years with my husbear, who's 30 years older than me.

I would insist on voice/cam chat and use that for a while before moving on to meeting the guy.
I could be wrong, but I'd assume the 50+ers were more aware of safe sex and stuff. Having lived through the 70-80s as a gay man surely left a mark.
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