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DATING DEBACLES - Flirting.com

Hilarious, Sometimes Painful Anecdotes of Careless People's Flirting Snafus

Maid of Honor Mayhem

Genny, my best friend of 16 years was finally marrying her boyfriend Kevin after four years of dating. As expected, I was to be her maid of honor. After spending months helping her prepare her wedding via phone and email I flew out to Kentucky to help her celebrate the big day. Of course I brought along my current boyfriend Jeff, a longtime friend of both Genny and I. After a long flight Jeff and I paid our respect to the bride-and-groom to be and then scooted off to our room to dress for the big combined bachelor and bachellorette party (yes, they planned the party for the night before their wedding). After endless hours of drinking, music, and dancing, it seems Kevin was getting quite flirty with another bridesmaid while Genny distracted herself with Jeff. Thinking nothing of it, I continued to go about my business on the dance floor; grinding up on all of Kevin's hot groomsmen. Eventually I lost track of Jeff, that is, until I found him making out with Genny in a dark corner. I was beyond shocked, drunk, and furious. Angry I ran around the room looking for Kevin and upon finding him prepared to make out with him. But just as I got ready to do so he pushed me away and I drunkenly fell down in front of a crowd of disbelieving family and friends who had only witnessed my spectacle and not that of the bride-to-be and Jeff. Humiliated I stumbled to my feet, ran upstairs and locked myself in the room for the night, leaving Jeff to fend for himself. I also booked a first class ticket, on Jeff's credit card, for home the following day, leaving Jeff dateless and Genny without a maid of honor for her "special day". Of course no one ever found out about Genny and Jeff, and I became the "talk of the wedding". Needless to say I have found a new social circle.

-Erin, 26

dating-debacles

Sorry Stripper Slips Up

For the past 10 years I have worked as an exotic dancer at a topless strip club. Overtime I worked my way from topless to full nude and back down to topless only. Needless to say a girl gets tired of the same old routine after awhile, but the money is good. Still, I wanted to get out, eventually. Well I started dating this guy Frank that I met at a local bar one night and after a few dates decided that I really liked him. He was the type that would hold my door and kiss my hand and order my food for me and stuff. I was afraid to tell Frank about "my job" so instead I lied and told him I was an aspiring actress and left it at that. All seemed safe until one night when we went out to a dance club. I got really drunk and apparently let instinct kick in. I began doing all these "interesting" dance moves, revealing my flexibility and a little skin at the same time. Frank seemed totally interested until a guy walked up and handed him a business card for a local strip joint, my strip joint. I didn't know what they guy had given him or why Frank looked so upset until he walked up to me and showed me the card. I was on the front, modeling my "pole skills". He just threw down the card at my feet and walked away. As I ran after him to try to explain I was confronted with a comment that was within ear range for Frank to hear, "Hey, aren't you that Lacy chick down at that strip club? Man, you sure get crazy with those poles!" Frank just stopped dead in his tracks, turned around and shook his head. Then he walked off. I've never spoken to him since.

-"Lacy", 31

Stuttering Stanly

I had been dating Sarah for four years and decided it was time to pop the question. I planned a surprise trip to England for our anniversary and planned on asking her on the curb in front of Big Ben where we had our first "European kiss" two years ago. What I didn't count on was Sarah having another admirer the whole time who coincidentally happened to live in England. The first night we got there she told me she wanted to see her longtime friend John. I had met John several times and always liked him so I thought nothing of it. Well things got sticky when she invited him along for our "premeditated excursion" to Big Ben. I tried to find a way to get John to give us a few minutes of "alone time" but he seemed reluctant. Determined to go through with my plan and thinking Sarah would find it admirable I would find the courage to do so I started to get down on my knees. Sarah just looked at me like I was crazy as I stood there stuttering like a madmen, unable to get the words out. As if that weren't embarrassing enough, it had rained earlier and the streets were slightly flooded and so, while on my knees, a car of teenage guys took advantage of the situation and floored the car through the water, soaking my stuttering self and howling at my foolishness. While Sarah just turned her head her "friend" suddenly came to her rescue and grabbed her hand, slipped down on his knee and proposed, just as I intended. OF course she said yes, to him, and not to me. All she offered me was a pathetic, "sorry", and she and John walked off to the hotel to gather her things. I have never been so humiliated or heartbroken in all my life.

-Jason, 27

Tasty T-bars

I had been dating this guy awhile but I was still really nervous about spending the night over at his apartment and stuff. He had two other guy roommates who were "typical" guys in the fullest sense and whenever we all hung out I became invisible as things like football, popcorn and beer became more important. Well one night I decided to be brave and stay over. To my surprise, when I got to his house his roommates weren't there. Apparently they had gone out for the night. Taking advantage of the situation, he and I hooked up right there in the living room. Halfway through our "nooky session" we heard his roommates stumbling up the stairs to the door. Quickly I threw on my shirt and sweats, stuffing my thong in the crack of the sofa cushions. A few hours later and I had completely forgotten about my underwear, until his friends went on a hunt for the TV remote and instead found my thong. After making a crude remark his roommate held up my thong for all to see. To make matters worse, the boys began to make lewd comments about how they were "dirty". Needless to say the guy I was dating was humiliated, though not as much as I was. Still, he was so embarrassed he kicked me out of his apartment right there and then and dumped me. To this day I can't show my face around any of them. I even dropped a class that I was taking that one of his roommates was in.

-Carly, 20

Sexy Surveillance

My boyfriend Mike loves his camcorder. He takes it everywhere he goes and documents everything; everything! After two months of dating we decided to step up our relationship. But after the first couple of times Mike kept insisting that we "document" our fun time. I wasn't so comfortable with the idea but Mike kept insisting that I could trust him and that he would show no one. He was my boyfriend so I assumed I had nothing to fear. Not until I walked into his dorm room one night and saw the whole male population of the dormitory viewing our little "sexcapades" as if they were the local Friday night entertainment.

As outraged as I was, I was far more humiliated. What's worse, walking in on their viewing only added to the catcalls and the humility factor. Needless to say I grabbed the tape and bolted. I broke up with Mike the next day. But with more than one tape of "evidence" I still have no idea to this day just how many people at my college witnessed me in my most liberal moments.

-Elizabeth, 23

Vertical Liaisons

My girlfriend Jenny's mom is really hot. I mean super hot. She's the type of single mom that spends all day making herself look good and then spends all night enjoying men complementing her on her efforts to look as such. I don't know if she's had plastic surgery or what but whatever she's doing is working. Lately I find myself constantly fantasizing about Jenny's mom, not Jenny. To make matters worse, her mom has caught me get "all stiffened up" when she walks into a room. She even called me out on it once to my embarrassment and her entertainment, with Jenny screeching, "Ewww! Brad that is plain disgusting." After giving me the silent treatment for four days she decided to "make things up" to me. She tried telling me that she knew a lot guys my age were attracted to her mom and that her mom simply relished in their attention so she understood my "accidental wood". What she didn't understand was when I accidentally shouted her mom's name at the height of my climax during our make-up sex session. She slapped me, got dressed, and left the room. She's never called me to this day. I can't say her mom hasn't though.

-Brad, 22

Nighttime Nooky Nipped in the Butt

My boyfriend and I had just recently convinced my parents to let him stay with us for several weeks before he moved into his new place. As I was planning on moving in with him, not wholly to my parents approval, it was hard enough to convince them to let my boyfriend and I stay in the same room together during the two-week interim. Nevertheless after avowing to "play it straight" we 'played it straight' as in the game of heterosexuality. After four night of being perfect angels, my boyfriend, and myself as well, we're going crazy. So on the fifth night while my parents were conveniently off in their bedroom what we believed to have been watching a movie, we began to take advantage of our rare moments of 'alone time'. Our make-out session however got a little heated and just as we had gotten our clothes off my mother walked in, forgetting or conveniently choosing not to knock and caught us just previous to our premeditated pounce session. Needless to say my boyfriend was asked to find somewhere else to stay and was given 24 hours to do. The next night he had to sleep on the couch, with my dad on the adjacent sofa keeping a skeptical eye on him the whole night long.

-Marin, 24

Chatty Cathy's Cyber Conundrum

I’m a 21 year full-time PR rep who is currently single and very, very bored. Unfortunately my job requires me to do a lot of 'off-hour' research at home and so to alleviate the boredom I often go into chat rooms to pretend as if I have a social life. SA if that weren't pathetic enough I was, at this point, a ‘cyber sex’ virgin. But one night, feeling rather lonely, and rather aroused, I got curious after a guy IMed me with a request for a "private chat, wink, wink". After playfully bantering for about three or so minutes our conversation launched into a full-time cyber sexscapade that was almost seriously entertaining. I don’t know if it was guilty feelings or what but we started talking about our families afterwards, replacing the whole ‘post-sex’ conversation ritual with cyber inquiries, only to discover that I had just had cyber sex with my best male friend! I mean this was the guy that I would constantly make snide remarks to about 'cyber sex' and sex-line addicts. Now who’s the pot calling the kettle black! Needless to say we had never hooked up before and it had never crossed my mind to even consider him romantically. I wish I could say that the hang-up didn't affect our relationship but after we figured out who each other were we simply could never really get past the awkwardness and have resolved to just 'phone conversations' until we get over our secret humiliation.

-Taylor, 21

Mamma Mia Mardi Gras

My mom has been divorced for the past five years. At 44, I would say she looks more than good for her age. She's one of those health nuts that works out all the time and eats healthy and has a body that turns the heads of even my buddies. I’m constantly being ragged on about my mom being a "MILF", and how much my friends would love to blank, and blank her. Obviously it's humiliating for me as a 23 year-old to hear such comments from my friends. All the same I figured my mom is a straight-shooter with a solid head on her shoulders so I have nothing to worry about. Wrong.

Last year when I told her I was going to New Orleans for Mardi Gras she looked slightly alarmed. My mom hasn't watched over me in forever so I just assured her I'd be safe, etc. But once at Mardi Gras I realized why my mother had seemed slightly worried. In the midst of one of the craziest naked mud wrestling beer chugging bonanzas I had ever witnessed was my mother, all slopped up and smashed, baring her bosoms to all! To make matters worse, my best buddy, who had mysteriously gone MIA for the past two hours, was standing their ogling her spectacle, and then making out with her when she would remember he was there.

I was too humiliated to say anything so I simply walked away. I never said anything to my mom about it and as far as my best friend goes, well let's just say we aren't as close as we used to be.

-Rick, 23

Fury of Flowers

One weekend my boyfriend had told me that he had to go on a huge business trip for work. I was really upset so he informed ‘my girls’ that he would be obliged if they would help keep me entertained. So together we planned a huge 'girls only' weekend bash. For Friday night we were to hit up one of the hottest local clubs and then Saturday we had managed to score a VIP list for L.A.'s infamous Viper Room. Sunday of course, was to be reserved for recuperation: bottled water, pedicures, movies, and ice-cream. Well what started out as the first night of 'girls just want to have fun' turned into a five hour romp with this really hot guy I had met on the dance floor… so much for girls only. After we had danced together, very closely, for more than an hour, we went to the bar where we shamelessly licked each other clean with several rounds of random body shots. Though my girlfriends were skeptical, and incessantly warned my drunken self to go home alone, I headed home with my new 'beau', who conveniently didn’t know about my old beau. As I drunkenly fumbled for the keys I heard the door unlatch from the other side. What was to be my nervous fiancé-to-be turned into a raging ex-boyfriend who caught me with my 'dance partner' hanging all over me outside of my flower bedecked apartment. My boyfriend was so upset that he threw the large 2 dozen boquet of roses in my face and handed the new guy what was to have been my wedding ring. After he stormed off yelling a few hurtful expletives I never heard from him again. To this day he refuses to take my calls.

-Jenny, 25

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