Question - The Gray Between Us: A Story of Friendship, Love, and Longing

So, I have this friend and I really like him. The problem is I’m gay, and he’s not. 100% straight-not. The thing is, we keep having all these moments where it’s weird. I swear he looks at me, and it doesn’t feel in a “just a friend” way. We get close, or he laughs at me and I go red, or sometimes I make him blush and he never gets embarrassed. What we have, it’s so special. I’ve known him for so long, we’re best friends. But I like him so much and every time I’m around him it’s getting harder and harder to look at him any other way. Sometimes, I think he looks at me the same, but it might be my pathetically hopeful imagination. I’m afraid if I tell him, he’ll get creeped out or something, and we won’t be friends anymore. I can’t lose him, but I also think he might say it back. What do I do? How do I ask without losing “us?”

Friendship is lovely. Love is beautiful. When you put the two together, what you have is the world. However, you’re correct; the greater the reward, the greater the risk. Some friends-to-lovers are somewhat planned; they were friends first to see how they fit together. “Let’s just be friends,” or “Let’s be friends, and maybe then…” These people have it easy. There are organic friends-to-lovers, where friends become close friends and then lovers. They’re the best, in my humble opinion. There are friends to gray to lovers. This is the one I’m most familiar with.

In middle school, high school, college, and after those chapters of my life, there has been much gray. High school is full of torrid, dramatic, intense, on-off, and confusing romances. I’ll skip them, and my apologies if you are in the higher grades of it. I’m going to peg you as college-age or someone in their twenties. I may be off, and I may tweak my advice if I am.

In college, I met someone who saw me at a club, and after a funny conversation, they asked me out. Apparently, they thought I was a looker and liked how I danced. We went on one date and immediately became close friends rather than a couple. We never talked about it; it wasn’t something to hide, but it was just “we had lunch at-”

Why? Who knows. We just walked out of the restaurant that way. There wasn’t a discussion of “just friends” or any awkwardness. It was as if we’d known each other for years. Sometimes, they’d crash on my futon in my dorm room. We’d be the first to talk about our romances, even if they were secret, with one another. We were never afraid to share our most embarrassing moments. Thanks to some electronic device (I won’t say what kind for the sake of guessing my age), we were glued to a screen when we weren’t together. They worked at a fast-food restaurant and always gave me free lunch with a wink. And I’d flirt with them; they’d flirt back, but neither of us knew we were flirting, or the other was flirting back. Our friends called it. We were suddenly very close. Like one of those TV couples that, after a few seasons, you want to yell, “Get together, already!”

They moved into my apartment after breaking up with a long-term lover after finding out that person had cheated. There was a spare room that became their bedroom. They’d cook me dinner, and we’d have some wine. We’d laugh on the couch and catfish each other’s horrible exes, taking turns. I’d score them VIP tickets to shows where I knew the promoters or directors; they were literally backstage, the works. Then we’d have those moments. We’d be chatting on their bed, and our faces were barely an inch apart. We’d look each other in the eyes and then lean away with a laugh. I’d slip into their bed without asking and without them saying “no,” and only one of us would be dressed. There were those shared bathroom/shower moments. I’d ask them about my club outfits, easily changing in front of them and ending up in the most revealing getup that makes me cringe or blush about now. If someone was dancing too close to me, or I’d try to step away from them or turn them down, this friend would get between us, telling the other person to back off, sometimes getting physical. My “friend” was a breakdancer and one of those people who didn’t look like someone on steroids, but they were muscular and intimidating. My friend’s exes, well, they incurred my wrath in other ways, in likely worse ways.

We were never official. We never slept together that way, but there were so many moments. It was a bad breakup. They cheated on me, and one would think, but you two never said, or perhaps thought, you were dating, but we played the parts. I kicked them out, and they treated me like an ex. Neither of us contacted each other after, even if we weren’t far from each other and had so many friends in common who, as much as they told us we were “together,” suddenly acted like we never were, probably so that way there weren’t sides. I had my breakup playlist, and it was the only thing I played. I have no idea what they did or if they pined for. However, one day, they showed up at my work. They lived across time, and when they stood before me, I was in automaton mode, shocked to see them. The encounter was transactional. They knew where I worked, stood in line, looked down, and seemed embarrassed, even though their showing up at my work and choosing my line was clearly intentional. and then left while I treated them like anyone else I would help, as though reading a script, and they left.

I only had one brief moment with them again. It was right before I graduated. They knew from others I was crossing state borders in the two-plus hours by plane way. What happened, or what did we say? I’m unsure, but they were goodbyes. We wished each other well. It was kind of sad. I invited them to my graduation party, but they wanted/needed to leave it there. When I came back to visit, we went to a club “not together,” but only dancing with each other. Blushingly, it was more bumping and grinding than dancing. Yet, as we were leaving, they picked up someone because they never needed to try. I had to sit in the back, and I mouthed off about it and had him drop me off at an ex’s. Neither of us reached out when I’d come for another visit, even though they knew I was coming home, and I knew they were still there. We didn’t speak for another five years. They no longer lived in the state, were married, had kids, and were visiting while I had returned home to live. They were visiting friends, and I reached out. They blew me off. They said they didn’t have the time, even though they did, and we both knew it.

Then, the opposite occurred. I’d moved out of state, and they tried to connect on social media, which I blew off initially and then responded, and it was awkward. We were in our mid/late twenties. They’d divorced and moved back home while I was dating the person I ended up marrying, and they reached out during our engagement. I didn’t see them for another eight years, when they wanted to, really asked in a near pleading way, to see us, knowing I was married and happily inviting my spouse along. Sitting there together, I didn’t know what to say. As excited and enthusiastic as they were, I was kind of just there. They were dating. We met again on our way back, and I was awkward again. My spouse did most of the talking. It was just so strange. We had so much history, very good and intimate, and then very bad, ending with each other blowing the other off when we visited home because we kept moving in and out of state.

I don’t think my visit will be awkward next time, and they’re excited to get together the next time I visit; they still live there. I’m excited, too, because I don’t think I’ll be awkward this time, and they’re far from awkward. We worked out, but it’s been decades of knowing each other, in and out of each other’s lives, intense emotions and moments, that TV couple who broke up, got back together, broke up, and then they were always dating or married when the other was single and all that awkwardness. Any romantic feelings ended when they first visited with their spouse and blew me off. Those feelings didn’t end because they blew me off, but like our first date in that restaurant, they were just gone. I believe any lingering feelings they may have had ended around or before that time. We’re not friends except on social media, but we’re not on bad terms, and I’ll see him the next time I visit home. I imagine it will be nice, and the only thing that has changed is we have truly moved on as just friends.

You and your friend appear to be in that gray, though with an added wrench of sexuality. It doesn’t seem like he is trying to flirt or be “awkward” on purpose as some men do, loving the attention and adoration a gay friend may have for them. It also doesn’t mean you’re an “exception,” or he is either curious or has moved away from the line of entirely gray. However, if you make a move and he is straight, and it’s just a friendship that has become intimate and gray, you’re right; he may pull away, and the friendship could change or possibly end. If he has feelings for you, he’s afraid of the same thing and probably questioning if he’s “changed.” You’re special enough that he sees past biology or is slowly moving away from that line that claims to be “100% straight.”

That’s not an answer, but there is no answer. It’s always situational, and every pair is different at their core, dynamics, and feelings. I can tell you to go for it, and it could go badly. I could tell you not to do anything, and you’ll miss out on the most wonderful thing that could happen. For what it’s worth, I believe people do or should love based on who a person is rather than their biological sex or gender identity. That said, I’ve always been singular, only attracted to and with a single biological sex and gender identity. My belief doesn’t change, but I don’t see myself straying from “what” I like. If he loves you enough as a person, I believe the worst case would be you both shrugging it off and forgetting about your confession, even if you don’t. I may be giving him too much credit, but that’s what I hope. I hope you two have that magical experience more because it is magical. Despite where my college “friend” and I ended up and our tumultuous history, we still had an amazing four years of magic that no one can dampen. However, we also intentionally left each other behind after and were in committed relationships when we entered each other’s lives again. We both know there will be no magic, but we don’t care.

I can tell you what you have is magical. Do you want to risk all that magic for even better, perhaps the best there can be, magic? Extraordinary magic versus losing your current magic? Is he and your current magic worth the risk of dying at the prospect of there being new magic you can’t even dream about? The most amazing versus none at all? These questions are not to deter you; they are the opposite. He may feel the same way and be in the same predicament of risking how you view him. He may like the idea, even if he never considered it before. He may dislike the idea, but you’re the same as you always were to him, or he may dislike it, and things will become “weird.”

I don’t have a crystal ball. Follow your heart because though you have all this confusion, all this risk, the heart usually knows. Don’t hope, and don’t feel despair when you look into it. Simply listen, without bias, to what it has to say. So much love, I’m sending you and him. I hope you find a fairytale, but if not, I hope you still hold onto your magic.

So Much Love (I’m pulling for you), M