One of the fun things about my gym is that I get to visit briefly with a hot guy in his mid-20's who works there every Thursday evening. I've seen him almost every week for the last two years, and I'm sure (though not certain) that's he realized I like him.

If I had to guess, I would say he prefers women, though we've never discussed it.

Every time we talk, he brings up the subject of money...in particular how little he makes and how hard he's always trying to make more. I've been tempted to say something like, "Oh, you poor boy, here take this", and hand him a couple hundred dollars on the spot just to see what his reaction would be. So far I've resisted the urge.

He did it again tonight, and it’s finally begun to dawn on me that he might be trying to get me to make him a job offer, so to speak. Am I imagining things?

How can I verify my hypothesis without getting into hot water?

I'd be interested to hear from anyone who's been in a similar situation.

I'm not really hung up on this, it just gives me something fun to think about.

...I've been tempted to say something like, "Oh, you poor boy, here take this", and hand him a couple hundred dollars on the spot just to see what his reaction would be. So far I've resisted the urge.

....How can I verify my hypothesis without getting into hot water?

Personally, I think it would be a mistake just to hand over money as a "gift". You could be setting yourself up to additional "payments" without compensation.

But, next time he hints, I'd ask if he's considered doing some odd jobs for additional income. Hopefully he'll take the bait and ask what kind of odd jobs. I'd then mention modeling, massage therapy, yard work, etc. and see how he reacts.

You might also mention that you've hired people before for a massage and they seem to make good money. That should be enough of a door opener that his response will let you know if he'd consider helping you with your "odd" jobs.

Hoover42,

If he's been bringing up the subject every time you meet for 2 years, then I'd say he's definitely hinting at something - the $64K question is, of course, what... If he is looking for a 'job offer' though, I'd expect some attempt on his part to outline his 'qualifications' or interest in the 'job'. Has he dropped any hints in that regard. As for your reaction, if you're thinking of giving him a 'gift', well this is the best time of year to do it, but I tend to agree with One Finger that asking him if he's considered doing/has done 'odd jobs' might be the better approach.

Reading your post though, I'm quite unclear as to exactly what your expectations are with this guy... I think before you do anything, you need to sit down and think through best case/worst case 'scenarios' about what kind of reactions you're looking for and where, if anywhere, you're hoping this might lead. Be honest with yourself, is your aim to get some satisfaction in helping out a potential friend, or are you actually hoping to get him into your bedroom/playroom/etc? Are you looking to form an emotional attachment, or just an exchange of pleasure for $$? I'm not expecting you to answer such personal questions here, but I do think you need to think about and know just what your expectations/hopes are before you head down this path...

Alan

Personally, I think it would be a mistake just to hand over money as a "gift". You could be setting yourself up to additional "payments" without compensation.

Ah...good point. Considering that I don't expect to be moving to another gym anytime soon, I can see where that could turn into a big problem.

But, next time he hints, I'd ask if he's considered doing some odd jobs for additional income. ...

Thanks for the suggestions, OneFinger.

Alan,

Hmmm, he has indeed always been talking about money, but he hasn't done anything to suggest that he's willing to provide something in return. I'm not very perceptive about these things, so who knows if I've missed any signals.

Yes, my message is a clear reflection of my vague thinking around this issue, isn't it. Thanks for pointing that out. I suppose it's a mixture of wanting to be helpful and also wanting to mess around.

You made a great suggestion that I should think about best case and worst case scenarios here, and I will definitely do that before going any further.

Thanks!

Say, Hoover, if you don't give the money to him, well, uh, could you, um, well, perhaps, send it this way?

You might consider asking him "Have you ever considered escorting?" If he ask what's that refer him to google search. If he knows what it is -- he has likely considered it. You can proceed based on his answer.

Say, Hoover, if you don't give the money to him, well, uh, could you, um, well, perhaps, send it this way?

Lucky!

Alanalt and OneFinger convinced me that I shouldn't do that.

Have you considered yard work or massage services? Maybe escorting?

You might consider asking him "Have you ever considered escorting?"

Wow, that would be awfully bold for me. But I see the merit of the direct approach. Have you tried that line with anyone?

Lucky!

Alanalt and OneFinger convinced me that I shouldn't do that.

Have you considered yard work or massage services? Maybe escorting?

Mr. Hoover, I could garden for you except that I don't have the right clothes. But for a massage I wouldn't need to wear anything, would I?

Well, Hoover, whether you send Lucky the $$ is upto you. But you can help the young man by sending him to me. When he next talks to you and broaches this subject, just tell him you know a fit middle-aged guy who enjoys spending time with fit muscled young men. And you can add that you know I'm relaxed about paying for my pleasures :-)

One think your port did not make clear....... have you seen him naked, such as in the shower or getting changed?

If the answer is yes, did he seem to flaunt his bod or was he overly modest? The answer to that might give you a hint of his preferences and you best course to follow.

Say, Hoover, if you don't give the money to him, well, uh, could you, um, well, perhaps, send it this way?

Lucky, I could send some money your way, but you have to earn it first...

The next time the young man starts to talk about money, why not just tell him, "Face it: no one is just going to give you money for nothing. Have you thought about things you could do to earn some extra money?" If his answer does not include modeling, massage, private personal training, or escorting, then he is not thinking about what you thought he was thinking about.

One think your port did not make clear....... have you seen him naked, such as in the shower or getting changed?

If the answer is yes, did he seem to flaunt his bod or was he overly modest? The answer to that might give you a hint of his preferences and you best course to follow.

E Gads. My spelling's getting worse day by day - although they are really typos!

[...] have you seen him naked, such as in the shower or getting changed?

Another good question, zipperzone. Hmm.

He just works the front desk; sadly, I've only seen him changing twice. He didn't seem modest like so many 20-somethings do these days (none of that changing underwear under a towel stuff). But no posing for me, either.

I think I'm beginning to realize that if the guy really wanted something he would have made it more obvious by now.

The next time the young man starts to talk about money, why not just tell him, "Face it: no one is just going to give you money for nothing. Have you thought about things you could do to earn some extra money?" If his answer does not include modeling, massage, private personal training, or escorting, then he is not thinking about what you thought he was thinking about.

I think you've hit it on the head, CharliePS. That question would give me a way to get my answer and not incriminate myself too much Thanks.

Based on what everyone else has suggested, I think I know what his answer will be.

E Gads. My spelling's getting worse day by day - although they are really typos!

I hate it when I do the same thing and discover that the expiration time on edits has expired.

I understood your questions, though. That's the important part, zipperzone.

Based on what everyone else has suggested, I think I know what his answer will be.

Well I sure don't and these posts definitely have me curious!

Since it's the holiday season, why not slip a little gift on his desk when he's not looking, and see which way the wind blows?

Merry Christmas

from your

Secret Santa!

Hoover42 to be perfectly honest I have never approached a guy in the manner that I suggested. My reason for not doing so is simply that I never pursue guys who are not escorts. I simply believe that type of pursuit, for me at least, is too much of a hassle. I want things nice, simple, and direct thus I stick to well-reviewed escorts on this site. There are more than enough hot escorts around to keep me busy and broke.

OMG, Lookin, I love it! I should do that...give him a fruitcake with $50 on top with a card signed "From your Secret Santa" :)

Hoover42 to be perfectly honest I have never approached a guy in the manner that I suggested. My reason for not doing so is simply that I never pursue guys who are not escorts.

That's the sensible way for sure, and I will probably chicken out eventually myself and just drop this; but my life is pretty boring otherwise, so at least it gives me something intriguing to do away from the computer. lol.

I think this thread is fascinating. I wish I had some suggestions to add. I think Charlie's suggestion is great!

I'd just smile at him and say, "You're a handsome young man. I'm sure you'll figure something out." and see how he responds.

I'd just smile at him and say, "You're a handsome young man. I'm sure you'll figure something out." and see how he responds.

That's the best response posted to date. You could also wink when you say it.