Possible New Relationship... Nervous...

So, I have this friend, my best friend. I'll just refer to him as Jack. We have been best friends for almost four years now. We talk about everything. We are very close. He knows I'm gay and is very comfortable with it.

Quick background on Jack. Jack claims heterosexuality, however, he has done gay things in the past and even talks about the willingness of him and I doing stuff together. And when I say "past," I mean when he was in Jr high, high school, and within the year (three years after high school). So, I would almost classify him as bisexual, but until Jack tells me that himself, ill respect that he is heterosexual.

So, here recently Jack has been bringing up questions such as "would we ever be in a relationship?" or "if we were in a relationship, how would the sex work?" I told Jack that I don't think we could ever be in a relationship. He asked why and almost seemed to be taken aback to me saying that. I told him that since he's straight, I wouldn't expect him to want to live the rest of his life loyal to another guy. Also, as a gay man, I have certain sexual desires that he probably wouldn't be comfortable with.

I did suggest that if it did happen, an open relationship would probably at least be an option on the table. At least to try it out, but that worries me and Idk if I'd be comfortable with going to other people for sex or him either. I am homoromantic demisexual. I need that emotional connection to desire sex and it would have to be with the man I'm in a relationship. If I start building a romantic relationship with someone else, I feel like that would be disloyal to my partner. Regardless of if we were in an open relationship.

What makes me think that he really wants this is that he kept trying to defend each "bad possibility" I brought up. And I do have a tendency to only think of the bad.

Now, should Jack ask me to get together with him, should I do it? I would only do it if he asked me, that way I know he is comfortable with the idea enough to take that step himself.

Please make note: he and I both share the philosophy of being friends with your exes. I am still friends with my last ex who cheated on me. He's a good friend, but a shit boyfriend. Because we didn't work out, I don't see a reason to completely lose the friendship we had before. That being said, I do feel that if the relationship between Jack and I didn't work out, we would still be friends after. Because we would both be going into it knowing there is a good chance we just wouldn't mix well.

Idk guys, I am nervous about the idea, but at the same time, I feel like I should at least give it a try. He is my best friend and we share a close bond. I mean, sex and the title "boyfriends" is basically the only thing we are missing from being together as it is. I just don't want to miss out on an opportunity if something good could come from it...

Sorry for the long winded question

 

Yeah, if they aren't super macho and are very comfortable around gay guys, straight guys will joke about doing gay stuff with me. He has talked about doing gay stuff, but he's not joking when he says it. Sometimes yes, but you know the jokimg tone your friends make. It will just be us and he'll say something out of the blue like "I'd let you suck my dick" or we actually had a serious conversation about if we did anal, if he could use a condom or not.

When we first became friends it was mainly "Jack," this other girl, and I that hung out all the time. He asked us both at this time, about four years ago, if we'd go out with him. He even told his parents that he and I were dating. We weren't actually though. So, no, this isn't the first time he's brought it up.

And yes, I've asked him why he keeps suggesting we get together. I told him that I don't think he would really want to be in a relationship with me for the rest of his life. Jack's explanation was, "we've been friends together for a while now and we just get each other."

In the back of my head, I'm concerned that he might be just trying to boost his ego by making his gay friend crush on him. But I also feel like that's my paranoia as well. I always immediately think towards the bad. Which is kind of the reason I'm posting on here. Maybe get a second opinion.

 

Oh yeah, I do really like him. He's goofy, charming, handsome, caring. All around a good guy. I told him many times that when I first met him, we were working at the same grocery store, I was crushing on him pretty hard.

When he got with his last girlfriend, we'll call her Jill because why not, I had to distance myself from Jill for a while. He thought it was a feud I had with Jack and Jill's play director. I didn't want him thinking that so I had to tell him the truth. I distanced myself because on some level I still had strong feelings for him and seeing them together made me very jealous. I had to back off until those feelings went away.

Now he's talking to me about how he is trying to end things with her. He says that he's not cut out for relationships, but every time he talks to me about breaking things off with her, the conversation goes in some way to him mentioning us be together...

Do you think maybe he's just tired of girls and wants a title so he can be with girls in our "open relationship" and not have to deal with the commitment.

Idk, sorry I'm a f'n wreck lol xD

 

Yeah, I believe I mentioned somewhere, I am not going to ask him to make anything official. I am going to wait for him to make up his own mind on if this is something he really wants. Like, make a PowerPoint detailing aspects of the relationship that he would be comfortable with and what would be a no go. Only after we are on the same page and its something we can both agree on would I even consider saying yes.

I'm just nervous because it IS something that I want and I want it to work. It just seems like maybe I'm looking to much into it, maybe it is happening and I'm just scared, or he's just testing his own boundaries and I'm the guinea pig.

I do believe, next time he brings it up, which will probably be the soon, ill speak with him about "if it did happen, what would be his expectations?"