Do I need to keep paying to feel this kind of connection?

[DunwoodyGuy]

On 6/16/2025 at 9:08 PM, MikeBiDude said:

Moderator alert/warning: let’s get this topic back on track, stop sniping, or this topic will get locked.

Please do!

[Wings246]

13 hours ago, lseactuary90 said:

people are attracted to what they are familiar with, so likely stick to someone who looks like someone they knew/know

I'd say this is a plausible generalization but a rather dangerous and limiting assumption.  I, for one, am not attracted to people of my own race and cultural background.  I even half-jokingly tell my friends that I "discriminate" against my own kind because I am bored by and tired of things & people that I am familiar and comfortable with day in and day out.  I want new flavors and territories to add excitement and different experiences to my stagnant life.

13 hours ago, lseactuary90 said:

There are also external prejudices e.g. 'would he fit in with my friends' / 'would he fit in with my family', etc that are made based on your appearance

Being gay is already not "fitting in" in the grand scheme of things.  So why should we force something that doesn't fit to fit?  I know in the perfect world, we want everything to fit flawlessly.  Things are already too difficult as is.  If I can find someone who fits me, I can care less if he fits in with my family/friends.  You may be looking a little bit too far ahead.

[lseactuary90]

1 hour ago, Wings246 said:

I'd say this is a plausible generalization but a rather dangerous and limiting assumption.  I, for one, am not attracted to people of my own race and cultural background.  I even half-jokingly tell my friends that I "discriminate" against my own kind because I am bored by and tired of things & people that I am familiar and comfortable with day in and day out.  I want new flavors and territories to add excitement and different experiences to my stagnant life.

Being gay is already not "fitting in" in the grand scheme of things.  So why should we force something that doesn't fit to fit?  I know in the perfect world, we want everything to fit flawlessly.  Things are already too difficult as is.  If I can find someone who fits me, I can care less if he fits in with my family/friends.  You may be looking a little bit too far ahead.

FWIW, I agree with all you are saying, hence I continue to be as I am, and do what I can. 

Ultimately, the question is: if someone is not even the slightest bit invested or interested in you (beyond sex) and you do not get these dating opportunities (regardless of reason here, we can probably spend days debating race and other things and still not get to the bottom of it, because everyone is different, has different 'preferences' and there is no real way of knowing what everyone wants), then there isn't much you can do. You can "force" someone to "like you" or "invest time in you". This is the question I am left with in therapy. We can basically continue to optimise how we look, work on ourselves, pick up hobbies, make friends, increase exposure through different events and people, and so on, but still if nothing lands (in a romantic setting), then you are stuck. This is where I'm at basically. 

Which ultimately takes me back to the thread's question - will I have to "pay" for intimacy because one will voluntarily give this experience to me? Do I spend countless more years "trying" and what happens if I turn 100 and it never happens for me? Do I want to look back and go "well I tried for 100 years and it never worked out" or do I want to try and at least experience something in my youth while I can? 

[+ Vegas_Millennial]

2 hours ago, lseactuary90 said:

will I have to "pay" for intimacy because one will voluntarily give this experience to me?

We all pay.  If not with cash, then with time, arguments, frustrations, compromises, freedom, etc.  So, yes, intamacy will require payment for the rest of your life 

[Archangel]

5 hours ago, Wings246 said:

Being gay is already not "fitting in" in the grand scheme of things.

At the risk of going off topic, this isn’t universally necessarily true. In New England, gay is as pedestrianly quotidian as it comes. It’s not even seen as a feature so much anymore…More important is political affiliation than sexuality!

 

[Muscleking]

On 5/31/2025 at 5:59 PM, lseactuary90 said:

I recently hired a masseur to come over for an erotic massage at my place. I also knew he escorts (he’s on RentMen) but contacted him for a massage on a different website hence it was a different rate also. Things flowed naturally - we ended up making out, grinding, and connecting beyond the massage itself. He was even down to top me (though it didn’t end up happening), and we ended up lying together, talking, and just being. It felt real. Comfortable. Honestly, it was the most “seen” I’ve felt by someone in NYC in a long time - definitely non-platonically.

At one point, while we were just lying together, he asked: “Why do you need to pay?”
I brushed it off. I wasn’t ready to unpack the reality of my dating life with him. The truth is: dating here has been non-existent for me. Literally zero dates. Hookups? Sure, but mostly disappointing - disconnected, drugged-out, disinterested, transactional. I’m more of a 1:1, slow, sensual kind of guy, and NYC’s scene feels like a conveyor belt of fast, flaky sex. Honestly, it’s been some of the worst sex of my life.

Instead of explaining all that, I just said: “It’s hard to find someone who can handle me.” He looked confused and said: “Someone tall, built, with a big dick like you? You’ll be fine.” But I don’t feel fine. That comment sat with me.

He also did go down on me, even though he identifies as straight. I didn’t overthink it in the moment, but it left me wondering.

I followed up a week later, and he was receptive. He messaged back quickly (again, rare in NYC), and was down to meet again. But then he said:
“No rush bro. But if I looked like you, I wouldn’t pay.”

That comment threw me. Not because I’m against paying as money isn’t the issue. What messed with my head is: what does it mean if the only way I’ve ever felt this kind of presence, softness, and intimacy is through a paid experience?

Was it him?
Was it just my starvation for connection finally getting fed?
Am I overthinking all of it?

I’ve never hired an escort before (just spa massages with HE's usually, although I have been topped there too sometimes lol) so I don’t know what’s “normal.” I do wonder if I should book someone else, maybe try a “boyfriend experience,” since I’ve never even come close to having a real relationship. Maybe I just need to get it out of my system.

Because here’s the thing:
In that space, with him, I melted.
I was soft, present, sensual, alive.
I liked who I was in that moment.
And that version of me doesn’t come out on Grindr, Feeld, Scruff, Hinge, Tinder or even at gay dancing or sex parties. Not even close. It was WAY better (in terms of that satisfaction and 'whole' feeling) than any therapy I've ever had also.

So I guess my question is:
Is it worth continuing down this road?
Will I be paying for intimacy forever?
And why did a paid interaction feel more real than all the “free” ones I’ve had?

Would appreciate any perspectives, especially from those who’ve navigated this before.

Mate, I’ve been there—truly. Sometimes the only place I’ve felt that kind of intimacy was in a paid setting too (and I’m married). It messes with your head, especially when it feels more genuine than all the “real” encounters. NYC can be brutal—cold, performative, surface-level. What you felt was real because you were finally met, seen, and allowed to soften. That’s not about money—that’s about connection. Don’t shame yourself for seeking it where it exists. Whether it’s through an escort or not, you deserve more of that feeling. Keep following what makes you feel alive. There is no shame in that.