Have You Ever: Had An Awkward Chat Moment?

Years ago on Manhunt, I sent an IM to this guy with a really hot ass. It didn’t take long for our conversation to move beyond the “hello” phase, as we began to exchange particularly naughty messages. At some point, we realized we hadn’t actually seen one another’s faces, thereby leading to the all-too-important step of unlocking private pictures.

And then it hit me like a ton of bricks. For the past half hour, I had been talking dirty with my ex-boyfriend. Technically, we had only dated for three weeks or so, but it got pretty serious within that short period of time. This may sound a little far-fetched. I mean, shouldn’t I have recognized his ass? And shouldn’t he have recognized my dick? After all, he had spent enough time bobbing up and down in my lap…

Yet I assure you this is a one-hundred percent true story. Other individuals have relayed similar stories about neighbors, bosses and church acquaintances, and each one is more awkward than the next. Hell, one of my friends tried cheating on his boyfriend, only to discover the person he intended to cheat with was, um, his boyfriend. It was kind of like the “Pina Colada Song”, with the exception being that they broke up in the end.

Have you ever had an uncomfortable experience like this online? Even worse, have you ever met up for a hook-up, only to realize you’re somehow connected with your potential partner? Chime in with your stories in the comments section, and we’ll all have a good laugh together!

– Dewitt

To see more pics of this guy showing off on cam, follow the JUMP:

(via I’m Live)

41 thoughts on “Have You Ever: Had An Awkward Chat Moment?

  1. Ended up meeting/dating someone who I later found out was the ex-fiance of a guy I had met on Manhunt… woops.

  2. Story of my life. I went to college at a smaller liberal arts school, I knew all the gays, and all the gays knew me. It was always awkward because I’d talk to these people online, knowing who they were, and then have completely different interactions with them in person. Even better is that these weren’t just students! I actually chatted with my bosses’ closeted boss. Needless to say, when the unlock happened shit hit the fan.

  3. Same as with Anthony.

    Freshman year, had a really hot chat with a guy at my school on mh, it spilled over onto aim, and it was about then that I realized that he was a friend of mine. Neither one of us was into the other irl, so there was that wonderful awkward moment where we were both like “so what now?”

    I kinda go out of my way these days to talk with guys on mh who don’t go to my college, but one in the area.

  4. The two guys who were looking to cheat on each other and tried to WITH each other, broke up?

    Sheesh… you’d think that was a sign from above that they were meant to stay together, and obviously both were OK with a somewhat open relationship even if they couldn’t admit it to each other. Some people…..

  5. Absolutely – was chatting with a guy and he ended up being my neighbor in the house across the street. I had my face visible and he didn’t.

  6. I was dating (having sex with a guy) and was getting along really well. It was hot and heavy. I kinda was falling in love with him. The problem was he was still living and having sex with his ex. We had a fight about it and I went out and found a random to have sex with. I didn’t care what he looked like. I just wanted sex.
    Well! My random showed up. Front door open and me naked on the bed with my cock in hand. Who was it but my boyfriends ex boyfriend. I said no to sex with him at the start but we talked and ended up in an all night fuck session.
    I never spoke to the guy I was dating again when he found out. I did however continue to fuck his ex boy friend for about a year after.

  7. There is a guy from my former school who was an ass to me. I found him on MH and he didn’t know who I was for the longest time because my face isn’t visible. He ended up apologizing and wanted to 69 with me. I would have but he found a boyfriend shortly after.

  8. luckily for me I tend to recognize someone from their pictures, so I’ll know to either pursue or avoid immediately…>.>;

  9. This occured on another site. I was traveling for work and felt a bit randy one night. So emailed someone who seemed like he was looking for the same kind of encounter I was; one night, no strings, safe and fun. He emailed back asking for a picture. I understand that, I get it. Faceless dick shots can lead to awkward situations: remember The Elephant Man had a perfectly normal looking penis. So I send this guy a face picture (just one) and ask for one in return. About ten minutes later I get a reply with his pictures. A cock shot, a picture of him in a pair of tighty whiteys, his shirtless torso…..all seems to be good….then the last picture……the grinning face of my supervisor from work. Yes, My BOSS!!! Yeah, so I got that sinking feeling in the pit of my stomach, and as soon as my mini panic attack passed I very politely typed out my reply “Nevermind….see you on Monday.”

  10. I had something slightly worse happen, when I discovered my boyfriend of the time and my ex-boyfriend had fucked each other on several occasions before I ever knew either one of them.

  11. When I moved back into the same town where my parents live a guy messaged me on here not realizing I was his boss’ son.

    That was awkward.

    It got even more awkward when my dad introduced us later, I had no idea what to say.

    Also, I only have face pictures on my profile, so sometimes I get the feeling people I meet have already seen me on here.

    One time, I met someone new in class and he got really nervous talking to me, and mumbled that if I ever wanted to study at his place. I definitely got the feeling he knew me somehow but I had no idea who he was. But he wasn’t hot so I politely declined.

    Last one: I had a one-night stand with someone after a very drunken night. That morning, he told me I had told him on Manhunt he wasn’t my type…

  12. Well this happened in the last fortnight.
    I had just broken up with my BF of three years and was and still am a little shattered by it. Anyway trying to move on i reactivated my manhunt account and started looking for something, friend, chat, fuck, anything really. After about a week i found out my BF had started seeing someone already and it turned out to be an old friend of his that had just come out of a 5 year relationship. So, angry and upset i went searching for a fuck and got a message from a cute young guy who wanted to chat and take it from there. I was very interested, but long story short after about 20 mins we realised that our recent ex’s were now dating and it just got weird, i think he blocked me after that. LOL

  13. Hell yes, for the longest time ive been getting hit on by an old bully who use to pick on me from elementery to HIGH SCHOOL!!!…… called me every name in the book and treated me like shit.
    The Son of a bitch dosnt recognise me and is saying he wants to worship my cock and ride me till the cows come home…….. O_o so yea waaayyyy to awkward for me, it aint happening.

  14. from another site went to chatting to texting didnt recognize him from pics different colored hair went to see him at the bar and he comes to sit down wit me and im jyst going wtf do i recognize you? turns out to be the bf of my hairdresser we just partied at halloween together not too long ago long story short… i now get involved with them both im now part of a threesome we r great friends even outside the bedroom with both of them.

  15. Some time ago on another site, I hooked up with three guys for some group action. It was a great time. One of the guys especially made an impression on me as he was very aggressive, cocky and a little sadistic in a harmless, mischeivious way. At the time I was extremely closeted, especially in business circles and paranoid about being found out. A few months later I was scheduled to travel with one of my clients, six or so people aboard a small company jet. One of the people was the CFO of the compay, whom I had never met, or so I thought until the guy from the hook-up walked up and acted like we were old friends. I kept my composure but I was nervous as hell around him the rest of the trip because he kept winking at me and making little comments around the others that only he and I would know what he was talking about. I would have enjoyed some more action with him, but at that point had to keep the relationship completely professional.

  16. Some time ago on another site, I hooked up with three guys for some group action. It was a great time. One of the guys especially made an impression on me as he was very aggressive, cocky and a little sadistic in a harmless, mischeivious way. At the time I was extremely closeted, especially in business circles and paranoid about being found out. A few months later I was scheduled to travel with one of my clients, six or so people aboard a small company jet. One of the people was the CFO of the compay, whom I had never met, or so I thought until the guy from the hook-up walked up and acted like we were old friends. I kept my composure but I was nervous as hell around him the rest of the trip because he kept winking at me and making little comments around the others that only he and I would know what he was talking about. I would have enjoyed some more action with him, but at that point had to keep the relationship completely professional.

  17. I found to chat with friends and a few family members that years didn’t see and/or never knew they were gay, and since I’m no shy and I show my face and my entires body naked, sometimes is ackward to talk to them when they say, “Hey, I saw your pics on manhunt”, or I try to hit them up by the site. It’s funny yet ackward. Curiously, I’ve never had sex with none of them, haha. XD

    What have been ackward is to hit up with someone of MH, fuck with them, and then found out who are they. When did happened to me, was in a open chatroom back at middle school. I hit up with a guy hwo was about to turn out 29, and wanted to celebrate his birthday. I was 15. So we met, he was gorgeus, and we fucked and had some freakin great sex.

    And few months after, I graduated and went to High school, just to find that he was a teacher!!

    When we both were in class it was ackward. And we were both shy, but as soon I stop having class with him, we start to chitchat in recess or after school, or take a coffee or something. He became a really good friend. We didn’t had sex again, just a few kisses from time to time. Now he has a boyfriend for a few years and they’re planning to go to Mexico City to get married.

  18. Wrong Mailing Address

    I met a guy many years ago, we had great sex and enjoyed each other. While he was getting dressed, I was looking over a magazine. Wanting to re-connect, I copied down the last name and address.

    Later, I sent him a card telling him how much fun that I had making love to one another. A week later, I received a card from his father, he did not tell me he was the “II”.

    So embarrassed.

  19. A friend Zed … desparately came after me week after week. Not my type ( VERY OVERWEIGHT and AGGRESSIVE ALWAYS). He was a counsellor working with my counsellor.

    I got rather pissed off he wouldn’t stop. He said – WE WERE MEANT FOR EACH OTHER. I told him I couldn’t see him anymore. He was not my type. And if he wasn’t my type – I couldn’t change things. He finally stopped calling when I refused his calls.

    A week later I’m acting in ANNIE! Huge $30,000 production. I met Xed. Totally mutually in hardcore in love but I was refusing to have sex! At ajoining mirrors for 5 weeks – smouldering infatuation. But until the ex moved I refused.

    He was living with his ex-lover/partner of 3 years. He swore it was over but couldn’t get him out of the house. A week after the show ended Jan 14th, Xed surprises me with a full paid trip with him to NYC for 10 plays in 8 days, and fun fun fun.

    He even went to my boss and asked him to let me off work for Feb 4 to 13. How romantic!

    It was magick. Until we landed in NYC. We got to a 5 star hotel – gorgeous!
    He couldn’t have sex. He said – he thought he would feel different as his ex was gone just the day before we left. So I waited each day. He rented a 2nd room and moved out on day 3/9. I called my brother across the country in tears and shock.

    We return home.

    Feb 14, yes! Valentine’s Day he told me I WAS NOT HIS TYPE. He decided this. We all know I was the swing man. Rebound! But at the time it was the first man to say I LOVE YOU! Love is blind. Hated Feb 14 ever since.

    March 31st. He is now full on in love and living with the very guy – Zed, whom I had said YOU’RE NOT MY TYPE. The irony was a killer. I wept for a week and took a 3 day weekend to recover and gain some balance.

    What was worse as we met over the next 10 years – I never saw him and felt any different. AND EACH TIME I KNEW HE FELT THE SAME AS WELL. HIS ACTIONS AND EYES WERE ALWAYS A DEAD GIVEAWAY. We knew it, I knew it.

    It was profound impression and very bittersweet. Unfortunately – he’s the only man who ever said I love you to me. So at 56
    and I wonder if I had fought harder to open him up to talk about his feelings and stuck with it – until he was ready – could it have worked. Making it work with words, listening was how guy #1 got my guy #2. I now know communication is everything.

    He’s been through a few men – but I’ve never been one of them. It took about 2 years to have even the confidence to go to a bathhouse I was so overwhelmed by the irony, anger, hurt and confusion. Maybe not the love of my life. But I believed him at the time.

    In short. I learned how not to be a rebound guy. That was worth everything. I wouldn’t say no to any of it again. The steam 5 months of love and infatuation were incredible. I regret only not working harder to get past my own feelings of hurt and rejection. And even that – well, we all do the best we can. When we know different – we do different.

  20. I’m amazed at all the naughty messages before the face pic. Awkward enough making the first move knowing most likely you’re gonna get an ugly face.

  21. See, I am mean. I would let him do all that, make him my bitch, etc. Then after he left, send him a text saying exactly who you are and what he use to do. Kinda karmic, if you ask me.

  22. hah. awkward story. but i was cruising around on manhunt one night, and came across a profile, everything seemed just fine, good body, nice endowment and could talk his way into anything, like my pants. So he comes over, great night, like wow. had me everywhere and anywhere he wanted to, real nice, chatted after, went home. Than.. the good part. My mother invites me to a christmas party and she’s talking about her boss blah blah, told him so much about me, he’s really looking forward to meeting me, and as soon as i turn around there he is, standing right infront of me, cool, calm and collected. and there i am just about to burst with laughter but there was a place and time for that. good times!

  23. So there was this guy who I used to hang out with for about five years consecutively off and on right after college. Nice guy, said he was straight. I didn’t care since at that age I was only about getting off and not so much about the stories. One Sunday, he texted me to hang-out for a nooner. He drove by, clothes came off, and we both got off. An hour later, I make a run to Staples when, lo and behold, I walk into my hook-up walking hand-in-hand with his girlfriend. It was the glue aisle, by the way.

  24. I have always feared this happening so while I am chatting I try to find out things like What High school they went to? home town? where they worked. The closet thing I came to doing was begin TXT’ing a guy who had a room for rent found out that he worked for a EMS service. Later found out he probably worked with my brother. (he also graduated same HS as me just a few years later) He could have easily told my brother and my brother could have told the whole family. Lucky after our hookup he took off really quick being in the closet he did not dare say anything. I wonder what I would do If I say him on the street somewhere, Ask him for another round or avoid him like the plague? I Still got his cell number. He was 23 and I was 33.

  25. Your last story just goes to show how pictures, no matter how good, are not a good indication about how attracted you will be to the guy in person sometimes. I have many times been surprised about how much better looking (and acting – if you take into account their voice, mannerisms, etc.) some guys are in person, or it could be the total opposite. Some guys are just photogenic and some are not.

  26. I caught my bf trying to hook up on this site a few times while I pretended to be someone else. All I ever do is to post a fake profile with a hot guy’s body pic and just wait for the bait to work. And he falls for the trick hook, line and sinker all the damn time. I don’t even do the first move. The first time I caught him, we actually finalized the deal for me to come over to his place. Needless to say, he was ashen faced when he saw somebody else instead of the one in the pic. LOL. We still had sex.

    (BTW, the following story happened before the first paragraph, to avoid confusion.)

    The biggest irony in this sordid drama is that he broke up with me because of suspicions that I was cheating on him (but I never did) and just one day day after the night of “the big fight” when I moved out, he was all over the net looking for sex. (Insert the first paragraph here. We had not officially broken up at that point.) I still feel like I was punished for something I never did but he secretly wanted to do himself. I did the fake profiles because I wanted to prove my point to him. Cowboyinbrla’s comment above particularly struck me because I was actually open to the idea of an open relationship, which I brought up with him not because I wanted to play around (I was completely satisfied with just him) but because I have witnessed first-hand how damaging the lies and hypocrisy guys have to go through trying to deny a natural biological instinct (probably half of guys I have hooked up with have bf’s/gf’s/wives) and because he himself has gone through relationships with cheating. I have no problem with my bf having sex with other guys if it’s not done behind my back with deception. It’s just sex to me; emotional intimacy, which I value a million times more is another thing. And he agreed with it, in theory that is. Ironically again, when I brought it up is when he started seriously suspecting me and began installing spy software on his laptop, checking my emails, etc. In hindsight, I realized I was maybe TOO honest too soon. It was the openness and forthrightness that backfired on me because he probably wasn’t used to it coming from a series of relationships that were full of deception.

    Anyway, even after the official “break-up” (after the 2nd time I caught him), we never really stopped seeing each other (it wasn’t even a week after it when he started wanting to have sex again); we just aren’t officially exclusive anymore. I recently brought up the possibility of an open relationship with him again and he seems a lot more relaxed and open about it now and is open to discussing it again. I think theory and practice just need to come together. And so the next chapter continues…

  27. I’m always afraid of finding my brother online. He’s gay also, and we both know that we have Manhunt accounts. We haven’t encountered each other yet, and hopefully NEVER ! I did encounter one of my family friends, but we didn’t chat because it’d be awkward.

  28. I live in a relatively smaller metro area, so these things happen more often than I can stand. I run into old hs (and even jr. high) friends, current friends, and even othe peoples boyfriends whose partner is unaware he’s on MH.

    Probably the worst instance for me was about three months ago… This really hot grad student contacted me on MH and turned the heat up on the conversation instantly. I was into it, but felt I knew him from somewhere. When we facebooked one another I saw we had a mutual friend together; a guy I drink with every week and consider to be a close friend. When I asked who he was, he told me the MH hottie was his ex-bf! Awkward! Throw in the fact he came on a little too strong and didnt always practice safe sex, it became a huge mood kiler for me. Lol!

  29. I’ve had an interesting MH encounter. Not so much awkward as just damn hilarious. So… I’ve been seeing this therapist for the past four years, and he’s gay. Well, I was browsing the profiles in my area on MH a couple of years back looking at the pics and I see a guy in this sleeveless leather jacket type thing. And the more I look at it the more I’m thinking I recognize the neck! It’s my therapist!

    So… I send the guy a message to probe the waters, ask questions about his profile, etc. Turns out it was him. He had no clue it was me! We eventually moved the chat to AIM and email, and it got pretty hot. We weren’t planning on hooking up, I’m only in my early twenties and he’s in his forties and wasn’t into someone my age, but we were talking about his sex life and how when he gets rimmed it really makes him want to get fucked and all sorts of things.

    Well, after awhile of chatting with him at night about erotic stuff with him thinking I was someone else and seeing him in session not knowing what I was doing I started feeling really guilty. So I came clean and told him it was me. He took it pretty well, wasn’t mad or anything, just said that if we were going to talk about sex, it wasn’t going to be online.

    We still have some great chats about sex in session, but unfortunately I don’t get to hear details of his sex life. And I never got to see a cock pic 🙁 But it was absolutely hilarious and we still joke about how funny it was that I found him on MH to this day. Ahh, the joys of small town living!

    Of course, he took down his MH profile so he wouldn’t run into anyone else he knew in a professional capacity!

  30. I’ve had an interesting MH encounter. Not so much awkward as just damn hilarious. So… I’ve been seeing this therapist for the past four years, and he’s gay. Well, I was browsing the profiles in my area on MH a couple of years back looking at the pics and I see a guy in this sleeveless leather jacket type thing. And the more I look at it the more I’m thinking I recognize the neck! It’s my therapist!

    So… I send the guy a message to probe the waters, ask questions about his profile, etc. Turns out it was him. He had no clue it was me! We eventually moved the chat to AIM and email, and it got pretty hot. We weren’t planning on hooking up, I’m only in my early twenties and he’s in his forties and wasn’t into someone my age, but we were talking about his sex life and how when he gets rimmed it really makes him want to get fucked and all sorts of things.

    Well, after awhile of chatting with him at night about erotic stuff with him thinking I was someone else and seeing him in session not knowing what I was doing I started feeling really guilty. So I came clean and told him it was me. He took it pretty well, wasn’t mad or anything, just said that if we were going to talk about sex, it wasn’t going to be online.

    We still have some great chats about sex in session, but unfortunately I don’t get to hear details of his sex life. And I never got to see a cock pic 🙁 But it was absolutely hilarious and we still joke about how funny it was that I found him on MH to this day. Ahh, the joys of small town living!

    Of course, he took down his MH profile so he wouldn’t run into anyone else he knew in a professional capacity!

  31. A few months ago I met this guy online..we ended up meeting…then he just completely disappeared for a few days. I was online again and found another guy…similar to the first nice looking and we clicked…only to find out later that this guy was a classmates, best-friend and roommates of the first one…and they were even ex-fuck buds! haha…so yeah!

  32. I had a couple experiences…lol One in particular was a super dl guy I chatted with on another site. The guy new of me on campus, but we hadn’t ever talked to each other in person. My pics were unlocked and he just had a body pic visible. He told me we went to the same school, but he wouldn’t give me his real name or unlock his pics. We chatted for a good 3 consecutive days until I realized that he lived 2 doors down from me. We both said we were going to the cafeteria and logged off and we both left our rooms at the same time looking awkwardly at each other…lol I doubt that he knows that I actually knew who he was to this day.

  33. Idk if this is the same kind of situation, but what the hey! I met this guy on a cam site. We moved it to IM and we had a c2c. All of a sudden, in the heat of rub one off together, he asks “so do u like girls?” i said yeah and then he replied “do u like young girls?” i asked him how young he was talking about and then he sent me a bunch of pics. i opened it and there were abt 15 pics of lil girls… =O I awkwardly told him i had somthing else to do all of a sudden. DEF closed my cam and blocked him. *GROSS*

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