Worst Online Date - Bad Date Stories

You want a bad online dating story!? Listen to this one: I once met this girl online and unlike many girls you meet on dating websites, she seemed really cool. We grew up in the same part of town, were raised with the same sort of family values and felt the same way about marriage and kids and everything. We even had similar likes and dislikes when it came to sports, music, movies and books. Of course when we were getting to know each other I thought this has got to be too good to be true, and as usual my instincts didn’t fail me!

We decided to meet up for a drink after work one evening. I should have known by where she suggested we meet up that something was fishy, but hey, hindsight is 20/20! Since she had no photo up on her profile, she’d described herself so I’d be able to pick her out (of course – another thing that should have tipped me off!) so I was looking around the bar for short brown hair and a grey business suit, when all of a sudden I ran into my step-sister. I went up to say hi and as soon as she saw me, her face fell. I asked what she was doing there and she just stared at me, speechless… and that’s when I felt like someone had punched me in the gut. There she was, my “date” for the evening, short brown hair and a grey business suit – my step-sister!

I’m sure you’re thinking we should have figured this out way sooner – trust me, we were more shocked than you could possibly be about that. But get this, after we laughed and lamented about it, she looked at me and said: “Well, you know, we’re not actually blood relatives.” I knew what she was getting at, but I just couldn’t go there – too weird! I’ve tried to get past her saying that since then but there’s still something funny about the way she looks at me sometimes – it freaks me out!

A few months ago I met Bill, this really great guy, online – at least, I thought he was really great! We went out a few times and were getting along really well. He was smart, funny, good-looking – the whole bit. Plus, he seemed really into me, and the best part: he wanted a long-term relationship (i.e. marriage). I thought I’d hit the jackpot!

Things were getting serious between us (i.e. I was starting to consider going to bed with him – something I’m not quick to do). One night, we went out for dinner to a great Ethiopian restaurant that my ex-husband’s sister told me about on the east end of town. Things seemed to be going okay until the server brought us our food and Bill wouldn’t eat his food. I asked him if anything was wrong with the dish, and he said that, the way the server had been holding the plate, her thumb was touching some of the food. I smiled and said “I didn’t know you were germophobic,” and he said “I’m not.”

Anyway, he lightened up and ate around the portion of food that the server’s hand had touched, and everything was going well until the bill came. We’d been overcharged on the wine we’d ordered, which is a common enough mistake, right? Well, Bill started going off about how they were trying to rip us off, and how they should even be charging us if they were going to be sticking their fingers in our food, and so on. I couldn’t believe it! He’d seemed so easy-going all along, and all of a sudden he was flipping out over one simple mistake? I was confused, and asked him what the big deal was and his answer explained everything about him: “I just hate how all n*****s think they can get away with stealing my hard-earned money.”

Well, needless to say, I now knew this guy was a racist scumbag and that I didn’t want to have anything to do with him, anymore. What I didn’t tell him, of course, was that I used to be married to a man of Ethiopian descent, and our sixteen-year-old son, Shawn, is half-black. So even though I am white, I took personal offense at what he said.

After the date, Bill suggested we spend a weekend together, away from it all. He said he’d surprise me with where we’d go. A few days later, Bill called me to say he’d bought tickets for next weekend to St. Lucia. He said he knew it was a splurge, but the money would be worth it. This was too good to be true, I thought: Bill was really going to get what was coming to him.

That weekend, when Bill came to pick me up, I showed him in to meet Shawn. Just as I’d suspected, Bill’s face when he saw Shawn looked horrified. He took me out of the room and started yelling: “What the fuck?! Why didn’t you tell me—” and I was like “What? That my son is half-black? It shouldn’t make a difference, you jackass!”

I was happy that he’d lose the cha-ching he spent on those tickets! And I tell you, nothing ever tasted so good on my lips as the smile I wore as I saw him huff and puff out of my house that day!

The last girl I met online had a big surprise in store for me. We went out a few times. We liked each other more with every date. Then one thing led to another one night and we ended up in her bedroom. She stopped me before I unbuttoned her jeans. She had something to tell me that she hoped I’d understand. I said okay—shoot. Out it came: “I have herpes.”

Gulp. Okay… I’m sure it’s not too bad. I see commercials for herpes medicines all the time. Lots of people have it. It’s easy to get it, no matter how clean the person you’re with is. So I’m thinking this doesn’t say anything about her. I mean it’s not like she’s some turboslut or anything, picking up diseases with every new guy she does. No, she’s a nice, normal girl who just had bad luck one time. But now what? Am I supposed to risk getting it myself? And I mean, I’m looking for a long-term thing here. What about our kids? Are they gonna be okay? How does it all work?

I told her I needed to think about things. She was obviously hurt but I had to be cautious!! I said I was sorry and that I wasn’t judging her or anything but she obviously was hurt. The more I thought about the situation, the more I was grossed out by it. I got home and read up about it on the internet. Sure enough it’s something that lasts forever. And you can get it no matter how careful you are. And it’s possible for your kids to get it. I even read on one site that it can make you impotent! It was just too much for me. I felt really bad but I had to call it quits with this girl. It was sad to break up with her over that, but I was happy she told me. Otherwise my buddy downstairs would be sorry!

I went out with a girl I’d met online last summer. I like to do things in style, so I told her I wanted to take her out to dinner at this fancy and expensive restaurant in our town. She sounded really into it. I picked her up at her place and she looked smokin’ hot—wearing a sexy red dress, stilettos, and the best accessory: her body. She said she’d always wanted to try this restaurant, that she loves going to fancy places and being treated like a princess. I’m into spoiling a girl, but only if she deserves it.

As soon as we get there, the maitre d’ greets us and get this, he says to her: “It’s nice to see you again.” Okay, weird—I thought she said she’d never been here, before. Then once we’re seated, she starts stroking my arm, nuzzles into my ear and says we should get a bottle of Dom Pérignon to celebrate our first date. I’m not really into spending an arm and a leg for champagne, so I said maybe we should get some wine, instead. She looked at the wine list and chose one of the reds at the bottom of the list—where the most expensive bottles are! Weird, again. Then, when the waiter comes to take our order, she orders the steak and lobster meal—the most expensive thing on the menu! Now I’m thinking—okay, what kind of a girl takes advantage like that on a first date? Like I said, I’m all for spoiling a girl, but there’s a girl who deserves it and there’s a girl who pushes things way too soon. That was the third weird thing and the last straw, and I decided that’s it.

I also ordered the steak and lobster. I then ordered a fantastic French truffle mousse for dessert and a glass of their finest port, too. Before the bill came, I excused myself to go to the bathroom. I headed to the front of the restaurant where the bathrooms are, and instead of going to the bathroom, I walked straight out the door and left her with the bill!

I made the mistake of going out with a guy who loved to party. We met online and I loved how wild and carefree he was. When we first started dating, we’d go out to bars and clubs together all the time, sometimes with his friends or mine and sometimes just the two of us. It was a lot of fun in those days—you know how it is at the beginning of a relationship—he was so exciting and I had a great time with him.

But those times never last forever. After a few months into the relationship, I started suggesting we do other activities together—like going to a movie or staying in together. But very time we started to make plans to go to a movie or something, we’d somehow end up at a bar again. He was still going as hard as in the early days, and the more I thought about the future, the less I saw him in it.

Any time I brought up Steve’s drinking with him, he’d say that this was who he was when I met him, and what did I expect? Plus, he called me a hypocrite because I like to indulge in a little pot every now and again, but just because I didn’t drink as much as him suddenly he was the bad guy. I mean, I don’t think smoking pot once in awhile is a big deal at all, because it’s not like it takes over my life. And I’m not against the occasional drink, which I of course indulge in, as well. But Steve never wanted to do anything but drink!
It was a tough decision to make—deal with Steve’s hard-partying ways for the rest of our days, or start all over again with someone new (and finding a new relationship as good as your last is not always a guarantee). But I said so long to Steve and have since been back on the market.

What do you do if you meet the perfect girl and she can’t stand to be around your best friend? That’s what happened to me when I met Tammy. For those of you guys out there who can understand this, Tammy was the perfect “guy’s girl.” This means she was into sports, she was no vegetarian and she had no problems going “south,” if you know what I’m saying. The only problem is, every time she got around my best friend, she started wheezing and sneezing and her throat would swell up and she could hardly breathe! Yep, you guessed it—she was allergic to my dog, Tyson. We tried everything to make it better: she took allergy medications that did nothing, we tried this shampoo on Tyson’s fur that was supposed to kill whatever thing it was she was allergic to in it, but that didn’t work either. We ended up staying at her place all the time but I’d always have to leave early in the morning to go home and feed Tyson and let him out to do his business. Plus, I started to miss my little buddy, and what were Tammy and I supposed to do down the road when we got more serious and started talking about moving in together? Tammy probably hates me for picking my dog over her, but a guy’s gotta do what a guy’s gotta do!

A few years ago, I met someone on a dating website. He was handsome in his picture and he had all the right credentials – in his early 30s, with a steady and well-paying job, and looking for a serious relationship. We started chatting every so often, and there were real sparks between us. So we started chatting more and more and soon, I couldn’t wait to get home from work every day to get to my computer and talk to him. I was like a schoolgirl, and I couldn’t wait to meet him. But every time I brought it up, he’d say he wanted to take things slowly and really get to know each other before we met. It was hard for me to wait but I had to respect his wishes. Anyway, a guy wanting to take things slow was actually a nice change from the usual!

After talking every day for over a month, I actually felt like I was in a relationship with this man, and possibly even in love. He said he felt the same way, and he couldn’t believe how wonderful it felt. I asked him if he was ready yet to meet me, and he answered with a question: “Do you really love me?” I said “Yes, I do.” Then he said: “Okay, then I think we’re ready for this.” Exciting!

I couldn’t wait, so we made a date for the next night. I knew he didn’t have a car so I went to pick him up at his place. I could hardly contain my excitement as I knocked on the door to his apartment. What’s worse is I could hardly contain my outburst when the door opened. There was my dream man, at the door, in a wheelchair.

My first reaction was surprise. But once I got past that, I was outraged! Now, I am a sensitive person and would never take anything out on a handicapped person, but I had been talking to this guy and falling in love with him for over a month, and he’d never told me this about himself, which I think should have come out in the very beginning! Plus, he said things that I think deliberately led me to believe he was not in a wheelchair. Like, I asked him if he was into rollerblading once, and he said “Yeah, I roll all the time :)”

I told him I was mad about him lying to me. He said he wanted me to get to know him before we met in person so I wouldn’t get turned off by the wheelchair, that it shouldn’t make a difference, and that I should still love him anyway. But I just couldn’t get past the fact that he’d kept this from me and led me to believe otherwise all along with no regrets! How was I ever supposed to trust him again? I’m still trying to meet people online, but it’s hard to believe anything anyone says anymore.

I told this one girl I met online that I liked blondes, and she said how lucky she was that she passed my preference test. We met after chatting awhile and sure enough, she had great, long blonde hair. We went out a few times and then on one date, I noticed that there were little specks of dark brown at the roots of her hair. I asked her if she was a natural blonde, and she insisted that she was, and that I was imagining things. The next time I saw her, there were no more dark brown specks. All blonde, again. I was kind of weirded out, cause sure I like blondes, but I don’t rule out dating a woman if she’s got brown hair, so why would this girl insist that she was a blonde if she was actually a brunette? How insecure did she have to be?

But that was only the beginning. With every new date we went on, I found out something new about her that added to the fishiness of her character. For example, I once suggested we go see the latest Austin Powers movie in the theatre. She said sure, and that she loved Mike Myers and all his movies. So I asked her if she’d seen the old classic, Wayne’s World, and she said of course. Then later on that night I jokingly said “Schwing!” to her and she seemed to have no idea what I was talking about, so I don’t think she actually saw it.

Sometimes she’d tell me one thing about herself and it would end up being a lie. (For example, she told me she was a staunch non-smoker but when we were out with her friends one time one of them asked her if she wanted a cigarette!) I had no idea who this girl really was, and she wasn’t giving me any clear indications. I’d told her that I was attracted to blondes, but the truth is, I’d take a real personality and a secure, confident woman over a fake (or real) blonde, any day!

So I started going out with this guy last summer—he was great and we were having a great time together… then things started to get physical and we started sleeping together. That was all well and good for a few times… then one night, we were fooling around and I started to go down on him. All of a sudden, the guy started going “whoa whoa whoa” and stopped me from going down there. So obviously things are not totally comfortable between us yet, and I can understand that… after all, oral sex is pretty intimate, and maybe he wasn’t ready for it yet. That’s cool. After a couple more weeks, I tried again… and again, got the same reaction! Now I was feeling pretty dejected—I’ve never been turned down when I’ve gone down!! I tried being understanding and asked him if he was okay, and he said “yeah” and I said for him to just relax and trust me, that there’s nothing to feel funny about and that he’ll like it (I figured maybe he was inexperienced or something). But then, he goes: “no, I don’t want you to go down on me” and when I asked why, he said “cause I really like you.” So I’m like “oookay, that’s a good thing!” and, tell me if you can believe this, he goes “no, I really like you and if we have kids, I don’t want my wife to kiss our kids with the same mouth that has had my dick in it”!!!!!!!!!! That was pretty warped, huh? I was so surprised!!! I never thought anybody could think like that. Anyone out there think that way???

This guy and I started going out after meeting online, and things were going great in every way until we ended up in the bedroom together somewhere around our fourth or fifth date. He was gorgeous and had a body that would make your knees melt, and the foreplay was great cause this guy knew exactly how to use his tongue! Then, off came his pants and down went my libido! He had a tiny little frankfurter where I was expecting to find a nice, plump Polish sausage! So sad! But I’m not a total bitch so obviously I didn’t freak out or anything, I totally hid my disappointment and we went ahead with everything, anyway. Talk about anti-climactic! I couldn’t get off no matter how he went at it so then I told him that I generally can’t get off from intercourse (lies!) and that maybe he should try something different. He did and he was fabulous! So there’s a plus on his side, and sorry to sound like Samantha from Sex and the City, but damned if I wasn’t badly wanting a big strong man below the belt as well! Well, since he was such a nice guy and everything else was going so great I decided to stick it out for a while and see if I got over little Frankie downstairs… but a girl’s only got so many orgasms she can give to a guy’s mouth and hands!!! I can’t help it but I just need a guy with a little more meat to offer—any of you ladies out there agree with me??

I thought the good thing about meeting people online was that you got to know them before you started dating them. Not always true—no matter who you’re dating, there’s always stuff that comes out once you’re involved enough to get hurt.

Take Sandra, for instance. I met her on a dating website that had otherwise proved unfruitful for months. Smart, successful and gorgeous, Sandra had it all. Including a past.

A couple of months after we started seeing each other, and about a month after we’d started sleeping together, Sandra and I started talking about our preferences… you know, in bed. I’m like a lot of guys—lesbians turn me on, I’ve got the “naughty maid” fantasy and I’ve never said no to backdoor access. Judging by what I knew about Sandra so far, I was guessing she was similar to a lot of women I’d known—secretly wanting to be dominated and spanked, secretly wanting to let out her raunchy side but needing to feel comfortable to do so. Little did I know, that wasn’t even the half of it.

It turns out my sweet new girlfriend was into S&M. Sure, she wanted to be dominated and spanked, but I believe the correct terms for what she wanted are “hogtied” and “flogged.” Now, I’m an open-minded kind of guy, I understand that sexuality is not as straight-forward as my fairly mainstream porn collection would lead a person to believe. I wanted her to be satisfied, too, so I listened and asked questions, and as she got into more detail about the kind of stuff she was into, I asked “How do you come up with this stuff?” and she said “Oh, I’ve been involved in the community.”

“Community?” I asked. I had no idea what was coming next, and you’d never have guessed it looking at the successful marketing exec sitting across from me.

Ever watched the show “Kink”? Well, the stuff Sandra started to talk about was straight out of that horribly disturbing Showcase show. A whole S&M community operates out there, holding parties where people go to have complete strangers violate them in the most Story of O ways. “Submissives” actually fill out forms at the door, indicating what types of acts they are comfortable having committed to them (you know, like “penetration in any hole is permitted; clamps and whips of all sorts are fine; my ass is open territory but stay away from my nipples”) and then a total stranger (a “Dominant”) takes them into a room and does whatever he or she wants to them.

As if it wasn’t a total nightmarish fairy tale, even as an abstract thought, I was learning that my girlfriend, my sweet and beautiful Sandra with whom I was falling in love, was involved in this stuff. Sandra had filled out these forms. Sandra had been led into rooms, hogtied by strangers, blindfolded and had acts I can’t even bring myself to imagine committed to her.

And horror of all horrors: she liked it.

Ugh.

Since then, I make sure to ask the right questions when chatting online.

What would you do if you met the perfect guy, fell in love, and then couldn’t even stand to kiss him?

I met Alex on a dating website. He was a highly-paid software engineer with IBM, good-looking, funny, the works. He was in the same boat as me—older, divorced with teenaged children, and looking to find companionship. We got along famously and were both excited to meet each other. A few weeks after we’d started chatting, we decided to go out for dinner together.

I bought a new dress, new shoes and got my hair done. I dabbed on some of my favorite, expensive French perfume and headed down to answer the knock at the door. When I opened it, I found Alex, handsome as ever, standing on the front porch. But as the door opened up, it air it wafted in from outside smelled of the garbage my neighbors had left out next to their garage. What a shame, I thought, that it had marred my first moment with Alex. Oh well, I thought, and invited him into the house. As I closed the door, the stale garbage stink stayed in the house. I thought: Wow, my neighbors really have some old garbage that it could stink that strongly. Oh well, I thought, it’ll disintegrate and disappear soon enough. I apologized to Alex, but he said he didn’t really notice it so I felt more comfortable. I smiled and thought, what a gentleman, and invited him in for a drink before we went to dinner. As we walked into the living room, however, I noticed that the stale air from the garbage was actually following us into the house! Gross, I thought, maybe it latched onto Alex’s dinner jacket and now it was stuck to him. Oh well, I figured, if it’s not bothering him, I shouldn’t let it bother me.

Half an hour went by and the stench only got stronger in the house. I didn’t know what to think! My mind was going all over the map to ridiculous ideas: maybe I had forgotten to apply deodorant and was very, very nervous; maybe one of my kids had been sick upstairs and the smell was actually wafting down from one of their bedrooms; maybe when I opened the door, some dying animal scampered into the house and is now rotting away under the stairs!

It was only after Alex laughed heartily at a joke I’d managed to squeeze out in the midst of my paranoia that I figured out where the smell was coming from! His mouth! That rotten, skunky garbage-juice stench was simply Alex’s disgustingly bad breath! Wow, I thought, I’ve never smelled anything so horrendous, and it’s actually being produced by such a beautiful thing sitting across from me. I went into the kitchen and brought out some scotch mints. He had one, and for a brief moment, his breath smelled a little minty… but it was as fleeting as my hopes for a romantic evening. How did I expect a little mint to battle the forces of evil hiding in his gums and under his tongue? How was I ever going to stand being around this guy, let alone kiss him, or anything else?

Needless to say, things didn’t last far past that drink with Alex. What a shame that halitosis is not something you can diagnose through an online relationship!