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Complicated situation, I'd love to hear your thoughts

dragon08

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Sorry I apologize in advance that this is a long post. I need to type this out and clear my head and hopefully get some good third party insight.

Ok so theres this guy that I have for class. I met him at the beginning of the school year but I never paid much attention to him because we never had to interact much until recently.

Starting about 3 or 4 weeks ago I started to run into him a few times and we made small talk and I didn't think anything of it. So then I had to play at this event for the university with the Jazz Band. The event was on a Friday night but we had to be there from about 1 pm to like Midnight. As it turns out, He was there as well because he was doing a comedy Routine as part of the entertainment.

At the event I started talking to him and we sat together along with a professor and his acting partner while we ate the lunch we were provided with. After the lunch we broke off from them two and we started talking alone.

While we were eating I realized that I thought that he was really handsome, and that I really liked his personality.

After we broke off from the other two, we talked and got pretty deep in conversation, he told me what he wants to do in life, what he's done and a bunch of stuff. (He already knew that I was gay.) Over the course of the conversation I found out that he is Bisexual. He was in the army for a few years and was in Afghanistan. He is 27 (I'm 19), he wants to direct movies and/or be an actor. (He isn't one of those half assed "actors" though. He has gone to auditions and he's been an extra in a legit hollywood film. And this is all within the last month or so of talking to him)

But he also told me that he has had a difficult past. He told me that he wasn't over his last relationship a few years ago. They were really serious to the point where marriage was a possibility. The guy that he was with died. As he was telling me this he looked like he was on the verge of tears and I just wanted to hug him and make it all go away. The look on his face broke my heart.

Our conversation got cut short by someone else but later on in the night he made efforts to try to talk to me while we both had free time. Afterwards I had to help put all of the bands equipment away while he was talking with some of the guests. By the time that I was finished helping he was gone so I couldn't talk with him more.

Later on when we had class we got to talking a bit. The class after that I ended up walking him to his class afterwards but I had to make an effort to catch him. I added him on facebook and I messaged him and we started talking more.

The next class he literally waited for me. I had to talk to the professor after class and he waited for me. I then walked him to his class again and we talked until literally the last minute.

We've messaged each other a lot over the past week or so. Normally at this point I would ask him out, but I'm unable to right now because this entire week I'm out of town. So all we can do is message each other. When I get back I'm going to try to maybe go out somewhere with him even if it's for coffee or lunch on campus.

I'm pretty sure that he knows that I like him because I've complimented him and told him that I think that he is handsome.

I've gotten a couple of mixed signals from him, but I don't know if they mean what I think they do. For instance, today we were talking but the conversation seemed a bit strained. I would have to keep the conversation going a bit, and he would take a long time to respond between each message. I thought that he wasn't all that interested.
BUT, then I found out that he was studying the entire time for this big test, and the second he said that he was finished studying, the conversation got much more easygoing and consistent. So I don't know if I'm reading things like that wrong. It isn't a lot just a couple things. He hasn't been rude, or blown me off in any way.

I do get really positive vibes from him and I think theres a chance that he likes me too but I'm not sure. The more I find out about him, the more I like him. I'm starting to get REALLY strong feelings for him.


I do have a few worries though, for one there is the age gap, we are both Sophomores in college but he is 27 and I'm 19. I don't know if he is just going to think of me as some kid or something. When he found out my age, he literally said "I feel like your Grandpa." He knew I was younger than him and I knew his age before he knew mine but that was his reaction to the exact number.

I'm a bit worried about the fact that he has gone through so much (Being deployed, losing someone he loves, working and going to school, Moving across the country and buying a house) while I on the other hand have had a pretty easy life just going to school on a combination of a scholarship, loans, and my parents money living in a dorm not having to work. (I am really thankful for all of my opportunities though)

I also think that he is more attractive than I am, and that he could easily have someone else. Some of my friends tell me that I'm full of shit saying that but they're my friends, I think they are a bit biased in my favor.

And finally the big one, He has literally told me "I'm still not over the last person I was with" in the first deep conversation that we've had. That was a couple years ago, and I understand that is a terrible thing to go through. And I know that I can't even compare to what they had, at least not right away. And I'm worried that he might try to compare us both. A friend of mine has said that I might just be the person to give him that last nudge he needs, but as hopeful as I am, I want to stay realistic.

I really like him. I don't know if I've ever had as strong feelings for someone as I do for him. I've never been in love. So I'm also a bit inexperienced in that sense as well.

I'm worried that either the situation is too complicated for it to work Or that I'm just going to get my hopes up and end up broken hearted.

What are your guys' thoughts?
 
I think he has already been honest with you about the situation. He is not over the loss of his boyfriend. When there was no break, but outside circumstances, it could take years. People in these situations often don't know how they feel and struggle with what they need and want. And, sadly (and I say this from experience), they tend to give mixed signals. He could like you and have nothing but positive feelings for you, but I'd suggest that until he can move on from his past, he is not a good dating prospect and you should not get your hopes up. If you can be his friend WITHOUT expectations for more, go for it. If not, I'd say put some distance.
 
I'd follow the no expectations route as suggested. Worry, if you must, only about the present and don't get caught up in the future. Life is more interesting when you allow it to unfold. You probably can learn a lot from him and vice versa. Best wishes.
 
I agree with the others' suggestions. I feel that he is very receptive of having you more than as a friend. I would pursue this further. I'd sleep with him and get intimate a few times if the opportunity arise. That's one sure way to find out his real intentions and test out your compatibility. And stop making the age gap an issue, get over it; he's not a teen anymore and he likes what he likes - he's been to war for crying out loud.

One beautiful thing about being gay is that guys use sex efficiently to find out your compatibility with someone else without any hang-ups. It's not like you need to date a girl a handful of times before she gives it up and then find out that the sex was lousy or that you've had better. Get intimate with him. Take him to bed. If he's hesitant in bed then that's a sure-fire signal that you are going to have problems going forward and you need to move on with other people. On the other hand, if you've had amazing sex, he is the one who will take this further. The sex either stops, in which case you found your answer about his hang-up about his previous relationship and you need to move on and date other people, or you keep hooking up and develop it however far the two of you want to go with it.

Be safe. Protect yourself. There is an increasing tendency now for people in your age group as well as his to go bareback sex when it comes to that; that's stupid. Use condoms. With that said, good luck.
 
Well I've kept talking to him and without me bringing anything up, he said that he wants to hang out together when we get back.
 
If you read through your post you start with the story of meeting a friend who is older and hitting it off. Then there's a couple of paragraphs about how much you like him and how much you're attracted to him. Then there are 6 paragraphs listing why a relationship isn't in the cards, including his comment to you that he's still not over his last relationship.

It sounds like you both need a friend. It would be better for both of you if you didn't have expectations beyond that.
 
You can't force a relationship on someone when they already said they weren't ready. If you like him a lot, be his friend, but do not have any expectation further than friendship. If a relationship is meant to happen, it'll happen. Otherwise, you gain a good friend, and he seems to be a nice guy to hang out with.
 
Well after thinking about it I've realized that i want a relationship with him and I'm gonna try for it. Obviously if he doesn't want one then it isn't going to happen, but i really like him and I'm not willing to just let him get away for lack of action. I've realized that i could not care less about the age difference, the difference in life experiences, and all that other crap.

I feel like he has shown interest, i am past the point of mere infatuation and I have genuine strong feelings for him which is more than i can say about half the people i "like".

I don't know if something has changed within him regarding tbe guy he was with who died, or if that is something that he'll ever fully recover from. I've received signals from him that he might like me too and if i think that i have a shot at being happy with him, even if i risk rejection, i have to try. I am not a coward so I'm gonna grow some balls already and try for a relationship with him. I'm not gonna just let him get away.
 
Good luck! You've had quite the semester, if I recall correctly about that guy you had a crush on at the beginning of the year.
 
Yeah i did, this semesters been hell i took on way too many hours, and i haven't been lucky in guys either. But i really like this guy and I'm gonna try for him.
 
Yeah i did, this semesters been hell i took on way too many hours, and i haven't been lucky in guys either. But i really like this guy and I'm gonna try for him.

Go for it dude. The worst feeling I've had are the lost opportunities I've lost on people I liked. Regretting that I didn't do something in pursuing a relationship in the past. Do something about it so that you won't have any regrets in the future. It sounds to me that both of you have something for each other but are just hesitating, which is so predictable in general to most people, me included.

Go for it and good luck.
 
He sounds like a really good guy... and so do you! Don't overthink this, invest too much emotion in all of this or scare him away with your intensity. The age issue doesn't appear to be a problem for him so don't make it one. Your appearance is likewise not keeping him away. Let the friendship unfold as it will, enjoy one another's company but don't hassle him about dating or being your boyfriend if he is not ready for that kind of commitment. Maybe you need to look for other guys to date seriously while maintaining the nice friendship that is forming with him.
 
Yeah Well he said that he wants to hang out and I get back in town tomorrow so I think that I'll get coffee or lunch with him sometime in the next couple days and if that goes well, on friday I'll try to see if he wants to go walking in this Victorian style neighborhood all decorated for Christmas and this Festival thing afterwards.

Unless he has some kind of date planned in that case I don't object :)

- - - Updated - - -

Oh and Thanks Orton, Journo, and Bruce. :)
 
Yeah Well he said that he wants to hang out and I get back in town tomorrow so I think that I'll get coffee or lunch with him sometime in the next couple days and if that goes well, on friday I'll try to see if he wants to go walking in this Victorian style neighborhood all decorated for Christmas and this Festival thing afterwards.

Unless he has some kind of date planned in that case I don't object :)

- - - Updated - - -

Oh and Thanks Orton, Journo, and Bruce. :)

You're welcome! Just remember to keep it cool. ;)
 
Ok so yesterday I asked him when he got out of classes and if he wanted to have lunch with me today and he said yeah.

This morning he surprised me by eating breakfast with me. I was eating with some friends in the school Cafeteria when he messaged me saying he was gonna get breakfast (I live on Campus and he Doesn't, so the cafeteria is my main food source). Thinking that he meant at home or something, I told him that I was already eating breakfast in the Cafeteria. Then he responded that he'll meet me there (I don't know if he usually eats there or if he showed up only because I was there). A little while later he showed up and I ate with him. He also asked if I could Help him move next week.

I ended up skipping my first class to stay with him longer, (I just had review, nothing important) and then we both went to our second class together. We were let out early and I stayed talking in a group with him. Then right before the next classes started the group broke off and he tells me "Hey don't forget to hit me up later" and I told him I wouldn't.

Later on after he got out, I picked him up and we went to this Mexican Buffet I really like (it wasn't formal or anything this was a semi/warmup date) We ate and talked for about an hour and a half. And I had a good time. While we were eating he asked me if I wanted to go see a play with him on Saturday. I told him I would.

There was also this really funny part, we were getting up to leave and I told him that I needed to use the restroom before we left and we both got up and Our server, this really old nice guy, comes up to him and tells him "hey There's Dessert too" and He tells him that he was full, the server tells him "No you barely ate anything just get some dessert" and they kinda kept talking as I walked away and while I was in the restroom I could hear the old man keep offering him stuff and Him trying to tell him no thank you. After I got out of the restroom I found him outside and he was just standing against the wall slightly defeated eating an Ice Cream Cone.
 
So far things seems promising.
I'm glad you guys enjoy yourselves.
Keep this up, but remain discreet.
 
Congrats. It's proceeding better than expected.

"Louis, I think this is the beginning of a beautiful friendship." - Rick (Humphrey Bogart), Casablanca
 
Ok so today we hung out more. I joined him in the library and read while he studied, and then afterwards he bought the tickets for the play. Since he bought the tickets, I'm gonna pay for us to eat Saturday (he doesn't know yet). Afterwards he took us out for ice cream and we went to this Christmas thing our school had. Afterwards i walked him to his car and we talked for a while.

We talked about a bunch of stuff and a few things i didn't like, such as the fact that he is neutral towards marriage equality, and that he doesn't like holding hands and kissing in public because he knows other people get uncomfortable. I told him my stance on the matters.

He also told me about the big thing he had with the guy who died. The story broke my heart i wanted to cry. Even thinking about it makes me want to cry. And in combination of today and yesterday i realized that he has gone through so much Hell in his life on top of losing someone he loves.

So today i realized this. What i thought i really liked was this image i had if him. BUT i still have strong feelings about the real him that I've gotten to know a bit more. Maybe not as strong as before but somehow this feels a lot more real. I also am pretty sure that he likes me and that he knows that i like him.

I'm going to let things unfold naturally and not push. Whatever happens happens.
 
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