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Dating: Missed Connections, Anyone?

(Photo Credits: Sean Cody)

Has a guy ever flirted with you, hinted he liked you, but then for some reason or other you totally missed it only to realize ten years later (I’m clearly exaggerating but you know what I mean) that the poor guy was actually trying to ask you out?

We’re asking because we stumbled upon a discussion thread about this topic and also because this happened to me many times, it made me wonder if it’s just me or if this is a pretty common occurrence. I think maybe at the time it happened to me I was afraid I was just reading too much into things, that maybe there really wasn’t anything in there so I brushed them off. Still, I end up thinking about what-might-have-beens.

In the thread, it was practically the same thing for them. One guy was confessed to by the guy he liked (this happened to me as well); told him, “I love you,” but the respondent thought his friend was joking only to find out years later that well, his friend’s feelings was real. Unfortunately, his friend is now dating someone else and they missed each other twice.

Anyway, another said a guy practically undressed and paraded in front of him for an hour with nothing on but “his tiny black briefs.” The next day the guy asked, “I know you’re gay. Why didn’t you try anything with me?” Regrettable indeed since he liked the guy.

Moreover, there was this one guy who said a “really cute guy” who worked in the café at his previous job “kept making eyes at him” whenever he comes in. One day, said guy asked him what time he gets off work. He simply said “hello” and “5” before he continued walking past him. He realized (with regret) the next day that maybe there was something in there and apparently this kind of thing happens to a lot of guys in the thread all the time (this happened to me, too, and I had the same reaction).

What about you? Any missed signal/missed connection stories? Share it with us in the comments section below.


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  1. Hunter4B

    Being a survivor of abuse often means that I am confused by my own emotion. I am often shocked or repulsed in a moment and then later when my brain has time to process it, I realize I might have had interest. I completely missed any sense of guy attraction until my twenties, when a guy started giving me HARDCORE signs of interest, and I missed ALL those too … by the time he practically groped me, I must have given him such a WHAT The heck reaction, he never tried to make contact with me again. I played that scenario over in my mind for years, and then after my girlfriend and I broke up, decided I would ‘try out’ men. The Internet was not a welcoming place then, and I was pretty unaware of hook-up culture, thinking I would meet, and date, and eventual TRY with a guy. All signs pointed to try, Try, TRY immediately. That led to missing that there were guys, just like me, looking for something more than a hook-up. I’m on a slow track, I talk, get to know someone, invest time, and chat, and then I give into the date. That tells a lot, sometimes before the date, I get invited inside (attempted hook up) or make out in the car (attempt). Sometimes, I don’t go online, because I know in that moment, I’ll be the pursuer (ATTEMPT)! LOL! It’s all good, I have met someone and he is going through a lot because of a recent breakup, he assures me he doesn’t want sex with a stranger, and honestly, I don’t care, as long as he continues to invest in me (we are far away). He is a MAN, he runs his life, he owns a house, he wants kids, he wants it all, I want him, and I want to make all that happen with him. However, honestly, each day that passes, I wonder if he’ll meet someone better for him? I wonder if he’ll be my missed opportunity?

  2. Wesley

    Ah, crossed signals. Years ago, I had a straight friend. He knew I was gay. He was from Savannah and was very charming. He would do things that I would have taken as flirting if I didn’t know he was straight. For instance … we were at a restaurant. I don’t remember what the conversation was, but he reached across the table and stroked my hair. Another time, we were at his apartment. I was sitting on the sofa. He sat in a chair across from me. He got up to get something from the next room and when he returned, he sat next to me, so close that our thighs were touching. Another time, I showed up early to his place. He needed to change his clothes before we went out. He turned away from me and proceeded to remove his pants. He got the pants down to his knees and turned around to remove them completely. He was standing there in his underwear as he put on his other pants. ANY gay guy would have been all over him. But he had told me he was straight. So I figured he was just being his charming Southern self. I never said anything for fear of losing his friendship, if in fact he was just being nice. He was adorable and I would have done him in a heartbeat. Did I do the right thing or was I THAT naive?

  3. Ben

    Missed out on the sex, not a date. Met the hottest guy I have ever had a date with one night as the bar was closing and he clearly want to hook up with me but I was all stupid newby so we exchanged phone numbers. I called the next day and he invited me over. I suggested we grab some food first, so we met at Olive Garden. The guys was as bright as a box of rocks and much less interesting, so by the end of our date neither of us were interested. Lesson learned: fuck em as soon as you canb

  4. Charles

    Yeah (doh!) This guy at work introduced me to his mother, who then told me that her son loves me. Well, I had no idea if this was true, or if her son (my co-worker) would have been upset at his mother for “spilling the beans.” My attitude was, he could have told me himself – there would have been a lot less ambiguity. In any case, it seems the moment is past – he’s still friendly, but since I didn’t react to his mother or to him (at least, didn’t react homoerotically), he figured I wasn’t interested. Or maybe he just decided “dating” a married guy wasn’t worth it, even if he DOES love me.

    • FreeSpirit

      Maybe he was told that you were not AVAILABLE (not just married to a woman). It could also be that you are much more interested in having an affair with other bisexual men like you (preferably married with women) than in 100% homosexual men like this guy.
      When I was 17 years old, I knew this straight-looking guy who, upon finding out that I had no (love) girlfriend, told me that I should get a girlfriend because it does not “look good” to be a man without a girlfriend. He then proceeded to hook me up with a girl (nice and well-brought but then I was 100% gay) although I was really interested in him (I knew he was bisexual).

  5. Matt

    I’ve had more than a few guys flirty with me and then run scared when I not only flirty back but offer them an open door to ask for what they want. It’s like they wanted to be clever clever and do the flirting bullshit but they didn’t have the balls to follow through.

  6. Jason

    I can never tell when someone is flirting with me, I always assume it’s in my head. Something happened with my straight best friend, he lived with me for a year a few years back. A few months after he moved in he sent me a text saying “I love you” and I didn’t respond. He had a girlfriend at the time & always introduced me as his brother to anyone we meet so I never thought anything of it. A few weeks later I overheard him & his girlfriend fighting about how he looks at me when he thinks no one is watching & then a mutual friend she thinks Mike is not straight that he is probably bi but because of his religious up bringing he would never act on it. He did drop some subtle hints he was attracted to me before & after the text but they were so subtle that I thought I was crazy to think anything of it. When I finally asked him about everything his only response was why did I wait so long. We are still friends & I don’t think that will ever change but I always think “what if…”.

  7. Jeff Banner

    My old roommate’s cute cousin lived in the same complex as we did and would hang out with us often. He dropped by one day when the roommate was not there and I was in the shower. He asked if I needed any help and I laughed it off. That was about 30 yrs and I still regret not taking him up on the offer to see what might have happened.

  8. Mark

    I was in college in the late 70s, and bought most of my clothes at one department store. Usually the same guy probably late 20s, waited on me. I had thought about cock but never acted on it.
    One evening as I was headed out to meet friends for dinner he showed up at my place with beer in hand. I told him I was gong out with friends and he left.
    Now I look back amd think how that could have been my first man on man expierence. Could kick myself

  9. luigi nonono

    Constantly. So many guys are so self-absorbed that they completely miss out on opportunities to date. Or they put up so many barriers that they prevent connecting. Like my Facebook “friend” who, when I said I would like to meet him, responded, “I don’t use Facebook for dating, only dating apps.” It seems like one or two generations acquired the false notion that you are supposed to have all kinds of rules and strictures about who you will date, though in the meantime, they actually behave like sluts. That is a sure way to end up single. Facebook is the ideal place for dating as you can actually get a sense of the actual person and approach them in a reasonable fashion, unlike exploitive dating sites and apps (like this one).

  10. Exmil

    Fuck… People flirt… I mean men flirt and drop hints? When did that start happening? You mean they flirt like women do? My oldest kid keeps telling me it happens all the time in my direction, everywhere and I never notice. Hmm., must not be too important to the one doing the flirting then if I don’t notice it. Guess I’m not missing much.

  11. R-L-S

    Of course I’ve had many missed opportunities to date/hookup with guys.
    One guy sat next to me while on the ferry to Alcatraz. His daughter (or I assume) was with him. He made eye contact and had his phone in his hand as if he wanted to exchange numbers.
    I froze because I was with my family who were not far away. The boy was FINE! damn, another one got away.

    Another time this guy (who is a friend now) told me that he “Loved me” over the phone. I was speechless.. I thought he was joking because he is the type of guy that make comments then says he’s joking.
    After that conversation I knew he was serious and he really did love me and I did love him as well. We are just friends know.

  12. MilfordHomo

    Scene open: Boston, mid-80’s, Me: working on laundry repair at a hotel, head first flat on my back in a big dryer. “Laundry worker” was 6’1, 160, bl/bl and a couple years older than I was- (he was mid 20’s) Caught him looking at me more than once, me at him more than once too. Had NO idea how to approach the subject. Tried some stupid line that he didn’t ‘get’. looking back, he did the same thing. Just that awkward thing going on. Would have done it right behind the machinery! Just didn’t know how to say ” I’d really love to suck your dick!”. Mike, if you’re reading this, it’s a perfect example of the missed connection. Scene close. or is it???

  13. Noah Nova

    It’s not easy knowing if there was such connections, however knowin that I was really rejected and not favored during college years so lack of confidence and being alone. Even now I’m alone because I haven’t found those connections.

  14. Tris

    About 20 years ago, when my first halting attempts at sex with men had left me freaked out, I fell for a new guy at work who was single and a bit younger than I. We became fast friends, doing lunch all the time and the occasional dinner at his place. One evening we were eating as best we could despite being constantly interrupted by phone calls from both his girl friend and my wife. It was like they were trying to break us up or something. Anyway, during a lull in the conversation and between the phone calls, he said to me, “You know, even straight guys have sex with each other occasionally.” I froze. Deer-in-headlights. I just stared at him, pretending I hadn’t heard what he’d said. The “offer” was never renewed. And, we’re still friends although we’ve both moved on to different jobs, so we don’t see each other nearly as much. My loss.

  15. Jim

    Yeah, looking back, I have missed a lot of those opportunities. In the “olden days” before the internet and the changes in society, making a mistaken move could have serious to devastating consequences. I had had bad childhood sexual experiences of an unique sort, such that by high school I was very wary of making any first moves on a guy that in any way implied sexual interest. As I look back, things could have theoretically been different—in some cases, if I had been a bit braver in taking the risk; in most of the cases, however, the times really needed to have changed first.

  16. Joshua

    There’s been a number of missed opportunities for me, mainly due to my nerves or being self conscious. One time on vacation a really cute guy was hitting on me in a club but the music was too loud and I really couldn’t hear him. The next night there was a really nice guy who kept hitting on me and he invited me back with his friends to his boat but I had to rescue my friend from another drunk (as she had a flight). Knowing what I do about her though (she conned me out of money the next morning) I would have ran off with him. I kept in contact with him for a bit but we drifted apart…..as for my fiend of a friend we never spoke again after that.

  17. THROATABUSER

    I am pretty sure I miss them all the time! Guys speak to me on here all the the time; tell me I’m sexy but I just figured they’re trying to have sex so I’ll blow them off. One guy even asked me out for drinks but I figured it was just a setup for sex so I declined not that I dont like sex, I do, alot! But I do knpw how men can be and I just dont believe in being someones play thing. So I play it off by just saying No thank you but I usually regret it later. Just because you never know who might be ur next great love!

  18. Dean

    I had a good friend i always thought was straight. I had a hige crush on him. One weekend he and i went on a trip to the beach and shared a hotel room. Thisnguy was fine as hell. We were both early 20s qnd it was the 80s. He came out of the shower bare assed naked and took to rush in getting dressed. I wanted him so bad, but was scared i was reading wrong and woild never have done anything to ruin our friendship. Fast forward to about 12 yrs….he was in town visiting (married and with kids). Wife was back home in TX. Ran i to him at the mall and we agreed to meet for dinner and catch up that night. Ended up back at my place and eventually in bed. Often wondered how oir lives woild have turned out if I had acted on his intentions back then….we are both in our 50s now and I still have a huge crush lol.

  19. Lukng4luv

    I’ve had guys touch my butt, tenderly touch my back as they walked by, and when I asked if they’d like to go out sometime?, They would say; I’m not that way! Or have guy stare at you, the entire time you’re in the same café. Every time you went there. I would approach him, and he’d look down, or the other way. Drives me crazy. The funny thing is, I use to be really shy when I was younger. And still am to some degree. I’m 60, but still love being with the younger crowd, that are very active. Like this young guy that works at one of the Grain Elevators I pull corn or beans out of. God almighty, knows that he made him GORGEOUS! And when I’m around, he draws cock & balls in the grain dust. But, I really can’t figure him out. Talks bad about Gays. We’re friendly toward each other at work, talk and joke. I’m going NUTS, cause I’d love to get to know more about him.

  20. Jer

    I would say that amongst many gay men This —- in that
    Would you with a friend do you respect your friend you took what he said is him being straight and didn’t act on anything else so there are a lot of outrageous gay men that will try and go after straight Gay guys & A lot do & look at it like a conquest
    …..and it’s ridiculous if somebody’s interested in a roundabout way- it’ll happen if it’s meant to

    I actually went to high school with a guy when I changed high schools -my JR year
    – it was an alternative school there was a lot of little “troubled youth” shall we say in the class and I’m not sounding insensitive but I only say it that way because there was ( Even though it was a small group maybe 15 in the class as a whole Few females They were Mexican but most of the guys were Mexican / Hispanic descent
    a lot of those guys that were in group home settings. Been in trouble with the law, Me and it just happened to be the only other white guy & only blonde blue-eyed guy and actually He was really good looking really friendly . & and Befriended me right away & we got to be friends and we began to hang out
    I just assumed he was straight at the time
    I felt I was – at least at that time

    again I mention this only because it wasn’t until I was 25 that I started questioning my sexuality
    so with that in mind
    But we would talk about video games and comics and just lots of guy stuff. But yes girls too
    —he was dating a girl in fact and he would talk to me about her and It just happened to be the he had a falling out with her and ended things . That same day later on that night and I happen to be at his place after school as he told me he broke things off
    And I did hapeen to be spending the night .
    & No NOTHING HAPPENED B4 all the assuming bitches ON HERE think THAT !!!
    Or otherwise …..

    But In Retrospect
    Yes I wish it would’ve happened he was a good friend and great good & yes He was Hot – (Def now when I think about it)
    But What happened was he started propositioning me
    We were just talking alone in his room That night
    & he started to ask me if I’d ever been with another guy
    if I ever had an interest in a guy ever and ….
    ……& Yes then out right asked me
    Would I want to be with him sexually and otherwise as well….

    Now when I think about it
    – sometimes
    I really wish I would’ve taken the chance with him
    Honestly even if I was in my mind Str8 at that time
    I have to say it is really nice & it was really nice be found attractive by him
    – I would safely assume
    And he was a nice guy too
    -he was really decent
    He was really very sweet and very charming and but a really good friend
    at least for the time being that I knew him ….

    So my take on this
    To everyone who has or who may have somebody like that your life
    I feel it would be would be amazing if Esp you took the chance if there’s a vibe of attraction

    It’s so sad to miss opportunities like that
    Esp when I’ve seen it now for what it is -in hindsight
    & Too since -fast forward from that to more present day more so
    But remember I was 25 years old – it took me about a year when I started questioning & started looking at guys to draw my conclusion of having an attraction to another guy
    I did start looking at them differently
    What sorta was prompting
    I think initially was I started lifting weights as a teenager- I was like 14/15 YO old
    -really kind of a skinny kid and wanted to get buff
    my father taught me how to lift weights as he had been doing it for years He got quite big
    He was a fan of Arnold Schwarzenegger and I think myself growin up when Arnold started making films like Conan and the Terminator and like there was cartoons like He-man amd comic book superhero’s like Superman and the Avengers X-Men , etc..
    I think boys see images of characters like that even if they’re cartoons but of guys that are very muscular built
    But my dad stopped because he broke his ankle years B4
    but I myself really started looking at men differently at the age of 25 …as I was really into working out . Worked at gym too at the time
    and I kept thinking -is this just appreciation for their body like body builders admire someone for their work on their physique??
    or was it more so having attraction to another guy

    I also think about when I started going to the gay bars and clubs
    There have been a couple of bartenders and other staff
    – that I knew from
    One club I frequented -practically lived there
    There was one guy over the past few years – we’ve seen each other out and about it online and I’ve known him since the Days of that club that’s been closed for over 15 years ago

    He’s a really nice ,very handsome & great guy
    & it’s sad because I wish I would’ve known in some cases to have taken the chance – like him …..
    I mean I think we always knew that there was an attraction i’ve actually seen this guy since the club closed years ago and we have said to each other in very recent online chats the past few years
    As he’s been out of a very long term relationship I’ve been single the last few years
    & when we’ve seen each other out at a club
    Or when we have chatted online very randomly over the last few years –
    We have both been like….
    Why didn’t we ever do anything? Like why didn’t we have a date
    Clearly we were obviously attracted amd im also under the under impression that we had done things when I had been there drinking at that club years ago and just don’t realize or recall
    we had been done some intimate stuff a few times
    ( & NO we did not hook up all the way
    To All you bitches that would assume two guys automatically would hook up sexually in a situation like that)

    but we were making out and other stuff -he says …
    But there’s been a few others I actually known too.
    Guys from online chats or Guys I met at a club or knew from a club
    & it’s funny
    I actually went to a movie just recently and I had this really handsome scruffy blonde guy sit down next to me and I noticed this fingers had bandages on two of them and I got to talking to him the little bit before they started the film
    It was at one of those at the preview screenings for a new movie and I noticed he had a bit of a stutter
    I don’t know whether it was probably cold or if he actually have a speech impediment of some type but just as I chatted with them a little bit for the film started to see Michael really nice guy that was on the side this instant connection because films were talking about that meant to mention to some girls done in front of us about I’ve been to a film the night b4 at another theater
    But anyhow we got to chatting about different films and as I sat by me he kept pushing his arm closer to mine on the armrest he moved his knee against mine and I don’t know those are late message queues it there’s something there or if you’re just like getting comfortable which I wouldn’t of been opposed to getting comfortable with him more so but I would say take chances if anything sometimes you may find that great guy & sometimes you can find yourself in very lonely times by not taking the chance …..

  21. Nathan

    I’ve missed connections all the time. Was at a conference and a handsome nice guy who was also with me wanted to leave his bags in my room as he checked out by noon and I had the room for 1 more day. We came back to the room in the evening and we both wanted to catch some sleep before getting the red eye back home. He slept on the bed, and I just stretched on the sofa. He asked me repeatedly to just sleep on the bed – which was next to him – but I thought that was awkward since both of us were married guys. On our 4 hour plane, we got seats next to each other. He rested his head on my shoulder the second half of the journey and while landing softly said, ‘I love you and will miss you’. I did nothing, just sat like a statue there. We changed planes to our destinations and went our ways at Newark and I don’t think I’ll ever get a chance to see him again.

  22. Greg

    I walked into a print shop in San Antonio one afternoon to make copies for a book project. As soon as I entered, I noticed a guy who was with another guy, and there was immediate attraction. The first guy looked at me apologetically, because he was with the other guy, and I tried to go about my business, feeling flustered by the attention. The copier jammed, and while I was fixing it, the couple left, and I never saw the first guy again. Like Mr. Bernstein in “Citizen Kane,” “I’ll bet a month hasn’t gone by since that I haven’t thought of that [guy].”


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