r/AskGaybrosOver30

Hi all, I was hoping to get this off my chest just because I don’t feel very good.

I hooked up with a guy back in March who was visiting from another country and it was great. Good conversation, chemistry, etc. we exchanged numbers and kept in touch over Grindr.

He messaged me a few weeks ago telling me he would be back in my city and that he’d be up for meeting up again and looking forward to it. So I made sure for him to let me know the dates and I would make time for him when he was here.

Cut to today, was just checking to see if I should message him to see if he knew what dates he would be here. Saw his distance wasn’t that far from me so I thought I’d message to see if he was in town.

I saw him online and thought I’d message him just to see. No response but it’s been a few hours and saw that he blocked me.

I sent him a text as I have his number but I’m not expecting a reply.

Now I know he doesn’t owe me anything, not even a reply but I found it so weird that he blocked me after the last interaction we had was about meeting up and also felt like a positive thing.

It’s now got me questioning if I had done anything wrong. I just find it so odd.

Anyone else had this experience? I’m sure a few of you have.

I came out from a long term relationship and flew to Mexico City to explore. In the morning i talked to this guy sex worker and decided to go in his room. I sucked his dick raw and told him to get condoms. I went doggy style and somehow I looked back before he entered and the condom was off. I told him I don’t fuck raw and he put another condom on we had sex different positions. As long i remember he didn’t came. After that he showed me his prep pills and send me via text a hiv test from end of March. I thought of getting pep but I got no proof he didn’t fucked me with condom. I try to play it over and over. I’m fucking scared.
I got some questions.
-Would i know if a condom is on or not while I get fuckt?
- if he came inside me would I noticed later if cums drops out?

I got a test scheduled in 3 weeks.

For guys who are bottoms, especially masculine or late-bloomer types, how did you get comfortable actually being seen that way by other men?

I’ve spent a long time keeping that part private, and I’m realizing the hard part is not just desire to bottom, it’s letting myself be seen and treated as someone who wants that bottom role.

What helped it click for you?

This one ended weird... or did it? I have no idea anymore.

We had an argument back in March, if you could even call it that. It was a discussion. He asked me why I didn't delete the apps earlier because he deleted them in November (we started seeing each other in mid-October and met via Facebook, actually, of all places). I said I don't know. I wasn't talking to anyone. But we didn't talk about being exclusive until December.

That was apparently it.

Haven't heard from him since March. We still follow each other on IG but he's been ignoring me.

I recently noticed he unfriended me on FB. Then, last night, he posted a bunch of memes about being single again in your 50s to his IG story.

I guess that implies I'm single again, too.

In retrospect, I feel like he was searching for a reason to end it and found one even though it makes literally no sense.

I thought the sixth time might be the charm for me, but apparently not.

As much as I want to be in a relationship and I love that life, I feel like I'm becoming a serial monogamist, and maybe it's better to be single.

I haven't brought it up to my therapist yet. Not sure if I want to because I already know what she's going to say, but damn does this suck.

It seems like everyone else has much more fun than I do in sex clubs. I just end up wondering around getting ignored. I usually have success on dating apps so I don’t think it’s because I’m extremely unattractive or anything.

Does anyone have tips on how to start having fun in these spaces?

Thank you !

There’s attraction, interest, all the things. But I’m generally a pretty slow mover into a relationship these days and any sign of them wanting to lock in quick gives me some pretty major ick…Maybe it’s because the ones I let in too quick in the past ended up burning me pretty hard? Do I have too much of a guard up? Am I doomed? Does anyone else feel this way lol

I was holding hands with my partner when a nearby neighbor yelled homophobic slurs at us. This person owns a residential construction company. I need to but can't let this go! What would you do? Im angry and want him to learn from this.

I will try to make It short. I was texting this Guy on bumble. We matched and he started the conversation. Everything went well so, since i was free this afternoon i asked him if he would like to meet in person today. He said yes. I proposed to walk in the park and then maybe go to a bar or a restaurant. He said It was too hot and he didnt want to be outside. I then proposed a bar and he said yes. I asked him what time would be ok for him and he said 8:00 pm. I said ok.

I got ready, made sure i looked handsome, smelled nice, etc.. i was on time but he wasnt there yet, so i ordered something to drink. 5 minutes passed. Then 10. I texted my friend saying i had the feeling he wasnt going to show Up. At 15 minutes i texted him saying i was already there. No response. My friend told me to leave and meet him, but i still was hoping he would appear. At the 30 minute Mark i texted him that i had been waiting for him and he didnt show Up, so next time would be nice to give me a heads up. I left.

Then i met my friend, i vented a little and then we where just chilling, having an ice cream.

Two hours since i texted the guy, he answers:

"Hey, my lawyer called me about my visa and i just hung Up on him. Sorry"

I kind of felt It was a cheap excuse so i did what i've never done: unmatch him. I know I make It sould more dramatic than it probably is, but guys dont usually find me attractive, so i always feel that i have to settle with whatever comes along. Actually a few months ago i would have given him a second chance. But now im tired, It feels disapointing to make the effort, put interest, and have nothing in return. I felt this was disrespectful and i think i did the right thing unmatching. However, my mind keeps telling me that im not enough to be this picky.

I dont know if It makes sense. What do you guys think? What would you have done in my place?

Sorry about the typos, english is not my first language.

My partner’s mother was diagnosed with Alzheimer and she’s rapidly declining and it is sad because she used to be witty, sharp and a fun old lady, also she’s not even 70. The problem is my FIL is in complete denial, we had like an awkward visit because he’s asking her to do things around the house with him and she can’t. She reached a point where she has to wear adult diapers and the entire house smells of pee because FIL is in denial about that too. The house is a mess.

I’m trying to be supportive because I feel for my partner. We hired someone to clean the house but my FIL stopped letting them in, they won’t come anymore. At the moment we visit weekly to clean and help out and help with groceries. Then he comes in additionally throughout the week and I come in one day a week on my own with cooked food and to try and throw out any old food because they often have mouldy food.

My partner’s mother has a sister who is older and she has multiple kids and multiple and grandkids and babysits for all her grandkids, she’s very sharp and from her behaviour you’d be shocked to know she’s 70. My partner was trying to have a serious conversation with my FIL about the support they need and how it is all becoming too much for everyone involved and he’s saying it’s his (my partner’s) fault for not being married with kids. We are engaged and getting married and my partner is having a lot of regret about not getting married sooner before his mom’s health declining. His dad said he wants nothing to do with it and it’s unfortunate because they are old people who are struggling and a lot of what he is saying is coming from him being upset about what’s happening.

I don’t know what to do, don’t think I explained myself well here either but a tl;dr version is my partner is depressed because of everything going on and is putting our relationship on hold (I know it’s not the most important thing right now) but given her rapid decline I think we should get married sooner than later.

Also I can’t say this to him because he’s suffering more than I do but all of this is draining. I feel for them and I am helping out for my partner’s sake I like his parents but coming every week being shouted because I am trying to throw away mouldy bread or I’m helping them clean or bring actual cooked food is draining. This will only get worse, I don’t know what to do.

I thought about some of my past hook ups. I've had mostly good ones, but there have been a few awkward ones too. For instance, one of my regulars I've seen for more than a year tried topping me on two separate occasions. On both tries he prematurely ejaculated every time his cock came near my butt.

There was a different encounter where this premature ejaculation happened while we were making out.

During those situations I felt disappointed, but now I find it funny that it happened. These two guys are both in their 50's and have experience with men. It all came as a surprise. Lol.

Y'all have any awkward moments or funny hook ups? Please share them.

My partner (28) and I (32) have been together for nearly 6 years and living together for 4. We’re engaged and planning to get married next fall. I’m the happiest I’ve ever been with him, and wouldn’t change a thing about our life together. My issues only really start to arise when I see how he gets treated in our very gay neighborhood vs. how I do.

I may be older, but am generally perceived as younger than him due to me being 5’8 and 145 lb and quite feminine/androgynous, while he’s 6’3, 250lbs, and built like a linebacker (I hit the jackpot, I know). Lately, he has gotten much more masculine (getting really into sports, lifting/bulking, butching up his dress/voice) and since we live in a gayborhood and he goes to a gay gym, he obviously gets a lot of attention for this.

Guys come up to him constantly at coffee shops, bars, or in the gym asking for his number. When we’re out together, he always gets approached first. I generally have pretty high self-esteem and like the way I look, but I almost feel like I’m invisible compared to him. As a result, he seems to have a much easier time meeting people than I do since there are more opportunities presented to him.

I’m not at all interested in becoming more masculine for male attention, but it feels like there is an imperative to do so when making friends with gay guys here. It’s like, being fuckable is a prerequisite for friendship, and due to the perceived “top shortage”, a majority of gays are searching for a masculine, fuckable, dom top daddy. Meanwhile I must look like a commonplace and discardable twink (I don’t identify with the term, but I think it's what most guys would categorize me as); an accessory to the dom top daddy who is more of an obstacle to overcome than a sexualized being in my own right. I know that this is mainly my perception, but it’s hard to shake.

I’m wondering how other non-masculine gays cope with this feeling without compromising a presentation that feels natural and comfortable for them?

I had no intention of meeting someone or getting into a relationship, but I met my boyfriend unexpectedly and ended up falling in love. My actual goal was to move out of my current city either to Europe or somewhere warmer in the US.
From the very beginning, on our first date, I was clear with him that I didn’t like living in my current city and that I wanted to move out soon. He agreed and said he would be open to moving. We also talked about finances, and since he makes significantly more money than I do, he agreed that he would take on more of the financial responsibility in the household.

Now fast forward—we’ve moved in together and split expenses based on our income ratio. However, lately I feel like he’s no longer interested in moving out of this town. Every time I bring it up, he either ignores it or avoids the conversation.

Another big thing for me is traveling. I love exploring new places, and since I met him, I’ve only traveled once because he’s usually too busy with work. It’s starting to feel frustrating because even when he has opportunities, like having a whole month off in January, he still doesn’t seem interested in making travel plans.

I’m starting to feel like he prioritizes things based on his own interests, while the things that matter to me—especially traveling and moving—get pushed aside or ignored. Part of me wonders if this is because he’s contributing more financially than me but at the same time, these were things he agreed to from the beginning. Now I’m left feeling confused and unsure whether my expectations were unrealistic or if he’s changed his mind over time. I don’t know who to blame—I just know I feel unheard and disappointed.

I’m in this rather shitty situation for a long time. I’m on meds due to a complicated issue to control my blood pressure. I’m in shape, fit and active but it’s an underlying plumbing issue that’s too complicated to explain here.

Ended up on ARBs in early 20s, that’s grown to ARBs, also include a low dose of a diuretic, calcium channel blockers and a cardio selective beta blocker - a real cocktail going on! All being monitored by a cardiologist etc etc.

Anyway, if I’m off them I get palpitations and my BP goes scary high, so that’s not really an option, and I’m finding either way, sex is just a joke, and always was.

I get plenty of attention, but I am just so bad at this stuff is hilarious. I’ll hook up, end up in bed, and then I’m making excuses and just want to go home. Or I’ll go in a date and end up having a real nice meal and taking for hours and going home. I had a lifetime of being called a cock tease, a time waster and all sorts of stuff, which I suppose from someone else’s perspective is accurate - I can’t really complain.

I basically have had one relationship ever, which was with someone who was superficially great, but a bit of a manipulative bully - so that went very well lol

Other than that I’ve had hook ups and dates, most of which have been utter disasters lol - I look at other people and it’s not like I’m jealous, more just bewildered by how they do so this dating and relationship stuff and so much of it lol - I can’t even figure out how they get the time!

Mostly, I’ll go on a date if I’m basically forcing myself to go rather than it being something that I actually want to do, and that’s becoming really annoying because people keep convincing me to try and try again and it’s actually giving me serious stress and I’m feeling just weird about it. I don’t really want to go on any more dates, and I’m completely fed up with unwanted pep talks from friends, and that is resulting in my friend pool getting rather smaller, so life is just tending to get more and more lonely.

Anyway, just kinda feeling like I am hanging up my hat and focusing on hobbies and stuff instead of putting myself though this over and over for no real reason.

Gonna try and keep this as concise as possible but there will be a TLDR at the bottom.

Recently, I (31M) met a guy (32M) on instagram and I think we’ve kinda hit it off. He saw my profile on an app but I never saw his message there. My instagram is linked so he messaged me there and pretty quickly had our first date. Since then we’ve hung out multiple times a week. I work 24hr shifts but pretty much any day I’m off, I’ve stayed at his place.

We aren’t official yet. He has said that we are mutually exclusive and dating but just not in an official relationship. He promised himself that he’d be single for a year after leaving a 7yr relationship with his abusive ex. We are definitely fudging that but he wants to stick with it saying we will be official in July.

I guess the challenge I’m having is I don’t know how to make our relationship special. It’s intimidating knowing they were together for 7yrs. I only came out 5yrs ago. I’ve had a couple relationships since then but nothing that substantial. With that, there’s not really anything we can do together that he hasn’t already shared with someone else.

I know a lot of this is my own insecurities. I’m just intimidated by all of his life experiences. He’s traveled a lot more than me, he has a pretty strong friend group, and has many fun stories. I don’t really have any friends since all of mine left when I came out. I spent my high school, college, and the first half of my 20s being a pastor. So I don’t really have anything fun to talk about.

I’ve even gotten in my head about our sexual relationship. I don’t really have a reason to think he doesn’t enjoy it but I’ve gotten bits of his previous experiences and I’m not sure if I really stack up. I know it’s dumb and wanting to be the best is a losing game but I do wonder if I’m really what he wants. I’m not small but I’m definitely not massive either. Also, I’m pretty short (5’6) so I know that’s neutral at best. I don’t know if his adventurous days are behind him but, if they are, that would make our sex life pretty dull in comparison.

Anyway, I’ve clearly failed at being concise but I’m just looking for some input on it all. Is there anyway I can make our connection special? Or do I just need to appreciate that he gives me the time of day? Am I just being dumb even asking this?

TLDR: Started seeing a new a guy and worried that I may not be enough for him. He’s had a ton an experiences including a 7 year relationship and it’s intimidating. I don’t know how to make our connection special and don’t know if I’m just dumb for trying.

I (gay M, early 30s) have been on three dates over three weeks with a guy (gay M, early 30s) I met on Tinder. I have disorganized attachment and a history of feeling unseen in relationships. I'm in therapy and currently doing TMS for depression, so I'm a bit raw emotionally.

The connection is amazing in person. The chemistry, the kissing, the way he holds me — it's unlike anything I've felt. He's respectful of my boundaries, physically tender, and we've gotten very close without having full sex. He told me he's always been reserved and has a flat affect — his face doesn't show much, and he's hard to read. He's in therapy too. When we're together, time flies, I forget my phone exists, and I feel genuinely calm and safe. He planned the first date, I planned the second, and he planned the third. We've consistently talked about wanting to see each other again at the end of every date, and we've seen each other every weekend so far. But after the third date, I knew he'd be busy the following weekend with a work trip and family visiting, so we didn't discuss when we'd hang out next.

His love language is music. He told me sharing music is how he connects. I made him a playlist — my first ever for someone — and he listened to it for hours, gave me thoughtful feedback, and said it was a solid effort. He's queued up songs I love in the car without me asking. Those moments feel intimate and intentional, like he's showing me he cares in his own quiet way.

But his texting and emotional style trigger me badly. After the first date, texts got more formal. He asks follow-up questions but it's sparse. He's consistent — he doesn't ghost — but he's not warm or effusive. I'm always the one leading emotional bids. In person, he's warmer, but I still can't fully read him. He's currently on a work trip abroad. He texted me sweetly from the airport, then landed — and silence since. I saw his dating app distance update, so I know he's been on his phone. It gutted me. I spiraled. I updated my app photos, panicked, changed them back. I'm lying in bed convinced he's just a nice, patient guy who tolerates me and maybe sees me as a friend. My last relationship ended with me feeling deeply unseen — I'm terrified of repeating that.

My questions:

· For those who've dated someone reserved, stoic, or with a flat affect — how do you distinguish "quiet love" (shown through actions, music, planning, gentle touch) from someone who's just not that invested or just being polite?
· How do I bring up a "where are we" check-in after only a few dates without sounding like I'm asking for a commitment? I don't want to self-sabotage something that might actually be real, but I also can't stay in this spiral.

Any perspective welcome.

If you had to give advice to someone entering a darkroom for the first time, at a party, bar, bathhouse, or sex club, what would it be?

I’m working on the next edition of my analog cruising manual and I’m fascinated by the different etiquette and cues people learn over time.

Hey peeps, looking for some advice.

I’m(cis male 36) recently single after an over decade long relationship with a strict bottom. I’ve always identified as vers and I’m bottoming again.

I used to be able to flip fuck all day long (admittedly I’m also much older than I used to be) but now I find myself struggling to cum after bottoming. I know this can be fairly common but I was looking to see if anyone has any advice to get myself back to being a vers king?

This also isn’t so much an issue of staying hard or losing an erection. I can stay aroused but that illusive big O is hard to find after my prostate gets worked over. Or at least that’s what I think is happening?

Not sure if men’s Kegel exercises help, or any other kinds of tips or tricks? It could also just be a sign of the times, and I top first, or have my top make sure I come during the act of bottoming itself…

Any advice is welcomed!

Hi, I was having sex with a fwb, I wanted him to cum in my mouth. Usually he would cum in my ass but this time he wanted to prioritize what I wanted… I assumed he’d jack off and cum in my mouth but he wanted to fuck me until he was close and then shoot his load in my mouth while I let sucking. I had read somewhere that that was unhygienic… and so I had that in my head, so I asked if he could get close, wash and then jack into my mouth. Which he was kinda a bit shocked by I guess and said “well I’ve been kissing you after eating your ass”. I think it killed the mood a little but we proceeded and he had a really intense orgasm in my mouth… but it got me thinking, what’s the go here? I take his point but it feels like there’s a slight difference of deep penetrated dick… I had also noticed a normal amount of speckled discharge on the sheets. Thoughts?

I’m intimidated by them. When I get sent pics on sniffies or the other apps they stop me in my tracks. I’m much taller than 6’3 and have a bear build.. belly and ass included. The guys that reach out tend to be more endowed. 7” plus. I had one tell me that big asses are made for big dicks. in a way I can see what he meant as a longer dick would get through meatier asses and still have enough left when it goes inside. But depending on position almost any size can get inside so he may have just been horny lol

I don’t know I just think it would hurt both length and girthwise. Or become difficult orally. maybe the picture angles make some appear larger than they actually are. All the dicks I’ve encountered in person have been 6” or less and it’s been wonderful. But I haven’t yet tackled one larger.

how have some of you gotten used to pleasuring larger dicks orally/anally in a way that feels good to you? For those that douche do you do it differently if the dick will be bigger

It’s a ridiculous problem to have, but it’s a bit of a mental block for me and I want to get past it

If there are past posts that talk about it, I can search deeper here.

I believe I come off painfully straight, I also have some neurodivergence that makes me carry myself in a bit anti social way (not awkward, but naturally more neutral and with a RBF, just not overtly open or friendly).

If I’m not in an explicitly gay space, and since I avoid things like Grindr, what are some tips that would help inform other guys that frankly gay and interested in meeting new people?

Or am I just a lost cause?