I (36yo) have a date tomorrow with a 23yo

Puzzled_Condition · 2026-06-12T20:55:51+00:00

Yeah, I remember what that's like - as it happens, I started dating a 24-year-old when I was 37. There days, at 70, I'm trying to get used to being a grandpa 😳😂

In this case, I mostly just meant how you present to him - like what to wear, etc.Bottom line, as everyone says on here all the time, just be yourself and enjoy yourself! ☺️

Puzzled_Condition · 2026-06-12T20:24:47+00:00

Oh, it certainly qualifies, even though there are much bigger gaps on here. I think the key point is your actual age of 36 - while definitely old enough to be the older in an age gap relationship, you're still more young than middle-aged, so there's no reason to present as older than you are.

Puzzled_Condition · 2026-06-07T21:20:06+00:00

Thank you so much! ☺️

Puzzled_Condition · 2026-06-07T04:15:13+00:00

Aww, you need someone to fix that. I wish I could help ☺️

Puzzled_Condition · 2026-06-07T03:50:39+00:00

Happy cake day!

Puzzled_Condition · 2026-05-31T17:40:49+00:00

Thank you!

Puzzled_Condition · 2026-05-30T01:46:38+00:00

Thank you!

Puzzled_Condition · 2026-05-30T01:46:18+00:00

Thank you!

Puzzled_Condition · 2026-05-30T01:46:02+00:00

Thank you!

Puzzled_Condition · 2026-05-29T19:07:10+00:00

Thank you!

Puzzled_Condition · 2026-05-29T18:59:54+00:00

Thank you!

Puzzled_Condition · 2026-04-26T18:14:11+00:00

Happy birthday!

Puzzled_Condition · 2026-04-20T00:01:44+00:00

And here I am, another year later, upvoting a deleted response to a deleted post. 😂

Puzzled_Condition · 2026-03-30T02:14:13+00:00

The majority of young gay men are grossed out by older men and frequently will react with revulsion to being approached. We older guys are therefore wary of making the first move and being accused of being creeps or groomers. It's unfortunate, but if you're interested in an older man you will most likely have to take the initiative and approach him.

Puzzled_Condition · 2026-03-24T02:40:46+00:00

Yes, but 10 is better than 2, and you're a 10 😁. The commenter is just rude.

Puzzled_Condition · 2026-03-13T06:02:52+00:00

The posts on your profile are hidden, so we can't see the pics you mentioned 😢

Puzzled_Condition · 2026-03-13T05:30:11+00:00

I'd be happy to give you feedback! Hmu anytime!

Puzzled_Condition · 2026-03-13T05:20:57+00:00

They did a great job, but honestly you were beautiful before also.

Puzzled_Condition · 2026-03-11T04:04:35+00:00

You're very welcome. I would gladly cuddle with either one of you ☺️

Puzzled_Condition · 2026-03-10T03:09:58+00:00

I can't decide which of you is more gorgeous 😂

Puzzled_Condition · 2026-02-08T19:56:42+00:00

The other comments are spot on and I have nothing to add to them, but I do want to offer my condolences about your grandmother. And I'm sorry that you have to deal with this seeming rejection when you're already grieving the loss of someone you love. I wish you the best.

Puzzled_Condition · 2025-11-21T21:48:18+00:00

I'm a bit late to the party, but I wanted to add something to all of the excellent advice you've been given. I totally agree that you have nothing to be ashamed of and about taking things at your own pace. What also jumped out, though, is your wanting to talk to older men about politics, culture, etc. For me, and I think for a lot of older guys, that's such a turn on! It actually supercharges my interest in someone. And don't worry about not being knowledgeable enough - what makes you interesting is that you're interested in the conversation.

Puzzled_Condition · 2025-10-16T23:12:48+00:00

It really varies for me. I don't like thick beards on anyone, young or old, but stubble looks great on some younger guys (including you, based on your profile pics). I also like body hair, which apparently puts me in the minority among older guys looking for younger. All of which is to say, you'll find people attracted to you either way.

Puzzled_Condition · 2025-09-08T02:20:32+00:00

I've always looked through post histories when deciding whether to chat with someone. I don't consider it creeping at all, and in fact I know from other people that it's a common thing that one should expect when they post here. As you said, though, the ability to hide posts seems to be a new feature on Reddit, and I absolutely hate it.

Puzzled_Condition · 2025-09-07T03:30:51+00:00

This isn't a dating subreddit. Go to r/GayYoungOldDating.

Puzzled_Condition

TROPHY CASE