Dating Disasters

Mastermind Weekend 1/16

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I'm Tina

I’m the owner of Carrots ‘N’ Cake as well as a Certified Nutrition Coach and Functional Diagnostic Nutrition Practitioner (FDN-P). I use macros and functional nutrition to help women find balance within their diets while achieving their body composition goals.

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Happy Thursday! :mrgreen:

This morning, I woke up craving this:

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I actually think I have an iced coffee addiction. Why is it so delicious!?! I thought I craved it because I was dehydrated when I woke up in the morning, but, a few weeks ago, I started drinking a huge bottle of water as soon as I woke up, but I still crave iced coffee. I guess there are worse vices to have, right?

To eat, I made a big bowl of oats + bulgur with blueberries, almonds, honey, and ground flaxseed meal. Mmm! It was GREAT combination of flavors!

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Last night, I attended an orientation session for Back on My Feet. I’m going to join one of their teams!!!

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To open the session, the Program Director asked everyone to introduce themselves and then share their worst dating story. I shared my infamous Stefan story, which I will save for another day, it’s more funny than terrible. I thought of a much better story on my drive home!

After college, I went on all sorts of bad dates. It was actually a running joke with my coworkers at the time because I always had the most ridiculous stories about the guys I went out with. You wouldn’t believe the plethora of cheesy pick-up lines I’ve endured over the years. I guess I attracted a lot of weirdos back then.

One day, when I was riding the T home from work, this really cute guy (we’ll call him Mike) started chatting with me. (I should have known right then it was too good to be true. In Boston, cute guys just don’t randomly talk to gals on the T.) We had a good conversation and he seemed nice, so I gave him my phone number before he got off the train.

A few days later, Mike called me to get together. He was at a restaurant downtown with his sister and her husband, and asked me if I wanted to meet up with them for a drink. It sounded fun to me, so I went downtown to meet him.

When I arrived, Mike was excited to see me and his sister and her husband were upbeat and friendly. Things started out really well. We were drinking and having a good time, but, apparently, Mike had a few drinks before I got there because he was absolutely hammered  and sloppy by the end of the night.

When Mike’s sister and her husband decided to head home, I used it as my chance to say goodbye to him too. I guess he didn’t want me to leave because he came running outside and tried to convince me (in his very drunken state) that I should come home with him. (Umm, let me think about that”¦ NO!) I hailed a taxi, got in, and waved goodbye.

Well, it didn’t end there. After I left, Mike ended up calling me 19 times and leaving at least 10 messages on my voicemail (Swingers-style). All of his messages basically said the same thing over and over again in drunken slur: “I can’t believe you left me”¦ I thought you liked me”¦ when am I going to see you again?” It was insane.

I never called Mike back because the whole situation bugged me out. I’m not sure if I should have given him a second chance or not, but I ended up hanging out with Mal again shortly after that, so it all worked out in the end!

Question of the Day

What’s your worst dating story?

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115 Comments

  1. I once went out with a guy who had a massive picture of himself in his bedroom, A-Rod style! ummmm, I’m sorry, but did you forget what you looked like, so you had to remind yourself every morning with the giant mural?? NO THANKS!! 🙁 haha

  2. I think my worst date was when we met up with a bunch of his friends, and one girl asked if I was the Heather that my date got his drugs from. Ummm, no!!!!! Needless to say that was the one and only date I went on with him.

  3. I’ve actually had very few flat-out horrible dates, but I do have one particularly bad story. Honestly, this wasn’t so much a ‘date,’ because I, for my part, was totally unaware that I was on a date. My freshman year of college, my friend (we’ll call him Chad) asked me if I’d like to go to a movie with him one Saturday night. To the best of my knowledge, we were ONLY just friends, and we’d gone to movies together before, so I had no reason to suspect that he had romantic intentions. Anyway, he picks the movie (“From Hell,” which was — seriously — about Jack the Ripper, and incredibly gory), then proceeds to put his arm around me during the opening credits. I was like, “What are you doing?” He laughed it off, kept his hands to himself, and not much later mentions that he feels sick. Apparently he didn’t realize that the movie would be quite so gory. Long story short, he rushes out of the theater, spends fifteen minutes outside (presumably taking deep breaths, hopefully not puking), and then comes back in and pronounces himself “fine.” I was pretty perplexed at this point, but we’d driven his car there, and I had no other means to get home. Anyway, not two minutes later, he grabs my hand (literally grabs it out of my lap), then leans in to try to kiss me. I pull away, tell him I’m not interested, then walk out of the theater. He follows me, apologizing the whole time, and then says that he’s content just to be friends. Fine. We walk through Target on our way to the parking lot, and he again tries to kiss me. Suffice it to say, I took a cab back to campus that night.

    To this day I’m not sure if it was his misplaced persistence that turned me off, or the fact he tried to kiss me after possibly getting sick. Either way, our friendship kind of tapered off after that night.

    1. random but did this happen at umass amherst? we had a target attached to the movie theater there haha

  4. I don’t really date, so I don’t have many stories. I hate dating with my soul and prefer to start relationships with people I already know. Probably has something to do with why I’m still single 😉

  5. My worst date was when I was in college. I had met this cute guy out at a club (first sign!) and we met up for dinner. He knew that I was in college because he picked me up at my dorm. In the middle of dinner he looks at me and asked me my age again. I told him that I was 19. He smiles and says, “You know, I’m old enough to be your father.” SAY WHAT??? He looked like he was in his early twenties but it turned out he was in his late 30s, yikes!!!!

  6. hahaha! that is a hilarious story 😉 Mine haven’t been too bad–just mainly really boring ones or once, after a few dates, a guy told me he wanted to marry me! It totally freaked me out! Now, I am happily married to the man of my dreams–you’re right, it does always work out quite nicely!

  7. Once a guy I was dating told me he was jealous of my dog (who was like 5 months old at the time) and couldn’t handle all the time I spent with her. Bahahhaha wtf! I know girls are crazy, but so are MANY guys!! I obviously ended that one immediately.

  8. Ahh, there are so many to choose from!!! I love all the stories.

    I once dated a guy and we went on a bunch of dates, but I was on the “take it slow” track and wasnt’ really sure about him. Well one night we were at a happy hour together and a casual acquaintance pulls me aside to tell me that he’s still living with his ex-girlfriend and that they are trying to work things out.

  9. I had a string of really bizarre dates during the time I was on match.com. The weirdest, however, was a guy I met at the mall for coffee. We had talked a lot on the phone and via email, so I though I had some kind of handle on him. He’s 15 minutes late. I’m chronically early. He doesn’t apologize, no bigs. We sit and chat and drink our coffee. Then he asks if I want to go and walk around and shop. Sure…

    He walks us into one of those tweener-type stores, you know, lots of super-tight, super-bright, teeny little things. I’m a low-maintenance girl who likes her jeans, NOT mini’s. Which was good. Because he wasn’t looking for me. That’s right, he was shopping for him. Kept holding up little sweaters and looking in the mirror, asking what I thought of this color or that style. I thought he was being a goof, so I played along for a couple minutes.

    I realized he was deadly serious, however, when he bent down to check something on a low shelf, and his shirt rode up in back. Two words: lace underwear. Everyone’s got their kink, but I was more than a little weirded out. I muttered the first lame excuse I thought of and ran like the wind!

  10. Haha, that’s horrible!

    I had one HORRIBLE date a while back. One of my coworkers tried setting me up with the guy who took my job after I was promoted, so we went out. We met at a brewery so he could watch hockey, he ordered a HUGE dinner, didn’t eat because he didn’t want to eat in front of me and then proceeded to steal the big glass beer mug he was drinking from because he collects them. I gave him a 2nd chance and the 2nd day was even worse with him blaring some raunchy music, speeding like crazy, smoking cigarettes in the car when I didn’t smoke, “FORGOT HIS WALLET”, then made me sit in the car for 30+ minutes after our date while he was in his brothers work trying to bum money off him to pay me back. He proceeded to ask me to a movie after where I just told him to take me home.

  11. Great post!

    I’ve had many many many bad dates. My favorite has got to be a client who I flirted with for months finally asked me out. I was excited. He took me to a restaurant, conversation was a little weird and got too racy for a first date! He plopped his wallet on the table and asked… i kid you not… ‘Are you gonna pay, or are you gonna earn your dinner?’ I tried not to act like i was completely offended…. but i paid not only for myself, but for him as well…. He drives me home, and I was giving him a friendly cheek to cheek goodbye, and he went in a totally different direction. He licked my face. Literally licked my face. And tried to impress me with his tongue ring. Needless to say, NOT impressed. Doesn’t even walk me to my door and i just shut the car door, he HONKS then drives away really fast. Last time I talked to him… EVER….

    1. Hahaha, ewwww! I’ve had someone lick my face before in a dance club… hopefully he got a nasty taste in his mouth cause I was all sweaty 😉 From dancing of course!

  12. I was meeting up with this cute guy from
    Match.com to have a couple of drinks. I’d already gone out with him once before so I figured he was at least a little interested. When we decided to change locations and head to another bar, he got a phone call and I heard him say ” wait which one is this? What’s your name? Yeah just meet up with us at the bar.” it was obviously another girl he was talking to from match.com. Turns out he was trying to find one girl for him and one for his brother!!! But both Odis ladies thought we were there to hang out with the same guy. At the end of the night I said to the other girl “you do realize what’s
    Going in here right? That guy is a jerk”

  13. I have too many to count. Not sure if I could even pick ONE.

    Okay…one guy said he’d take me to a “little Italian joint” he loved. I was imagining something a little more romantic than….OLIVE GARDEN. Um…

  14. I went on a date once with a guy who had a foot fetish. After dinner all he could talk about was wanting to rub my feet, and not in a nice gesture way but in a creepy I wanna get off to your feet kind of way. To each their own, but that certainly wasn’t for me!

  15. I once went on a blind date in college. It was a casual lunch date, he said he’d be wearing jeans and a sweatshirt from our college. Great…I’m sitting outside the restaurant and this guy wearing speckled black and white wool pants, a pink dress shirt, suspenders and a striped tie asks if I’m “Kathleen”… I freaked, but felt trapped. He said he wanted to “surprise” me by dressing nice. Hahaha! The 80’s called and they wanted their outfit back. He was a financial planner and took it upon himself to run to his car to bust out his briefcase filled with brochures. He then split our lunch bill and told me how much I owed and how much tip I should leave. He then took the reciept so he could “write off” our date. Awesome!

  16. I was set up on a date with a friends roommate. We went to a movie and home after… the guy was not interesting to me at all and we had absolutely nothing in common. The worst part of the night was as I was leaving he asked me if I wouldn’t mind tossing the trash by the curb on the way out… I was mortified! Toss the trash??

  17. Stefan? that is an Romanian name!!! 🙂 was the guy from Eastern Europe? please tell me details!! 🙂

  18. Oh my gosh, these are all so funny….had me in stitches! I can sympathize that almost all of these horror stories are from online dates, and I’m afraid mine is no different…

    This guy picked me up from my apartment (silly, naive me) and as I go to get in, I realize that the entire front seat is COVERED in trash. Garbage! He makes a hasty attempt to sweep some of it off, mumbling something about it being his “friend’s” fault that there is garbage everywhere. Right. So we get to this restaurant and he brought up sex, religion, super radical politics…everything you *don’t* want to talk about on a first date. When he asked me if I smoked and I said no because my dad had been a long-time smoker, he got up to have a cigarette anyway while I waited inside! Thankfully he realized that this was a bad idea and paid quickly, but still made me wait outside in JANUARY while he smoked. To top it all off, he asked me where I wanted to go next, and when I said that he should just take me home, he asked if I wanted to smoke a joint on the way, then offered to be my drug dealer. Hah! When I refused to let him walk me to my door, he sent me a text saying, “Shucks, no goodnight kiss?”

    WHATTTTT.

  19. uuuugh these stories are painfully hilarious! there was a guy I was friends with in college. I guess you can’t ever be “friends” with a guy in college. Anyways, he wanted to get dinner. He picked me up in his sweet ride, but the place was literally less than a minute walking distance from my dorm. Maybe 50 ft. Then when he dropped me off…again the fact it was so close is just bizarre…he said “So we’re boyfriend and girlfriend now, right?” This was all followed by a few weeks of him sneaking into the dorm to drop off flowers and huge 24oz cups of smoothies. Another ridiculous date I had was with a guy who picked me up at my dorm dressed as Hugh Heffner. I think that might have been a frat prank. But it is still ridiculous.

  20. I have a ton of awful dating stories. But my favorite story was that this guy who played football at my college and went pro (in fact all of you Boston Patriots fans probably HATE him) was flirting me up and trying to get my number and get me to go on a date and he told me: “You’re so pretty. You look like a female wrestler.” Me: “uhhh…excuse me, a female wrestler?” Him: “Yeah, like a wrestler.” Boom done deal right there. Note to all men…never tell a girl she looks like a wrestler. That is not a compliment in the least bit. He proceeded to get my phone number from one of my friends and called me ALL the time. Sorry, buddy, you may be an attractive football superstar, but I will never forgive you for telling me I look like a wrestler!

  21. These are cracking me up!
    My first date ever, I was 14 or 15 and the guy asked me out to dinner. He was a few years older than me so I was pretty flattered and geeked to go out with him. Well I get in his car when he comes to pick me up. He looks at me for a moment then says “You got money, right?” in this very rude voice. I assured him I did have money, so he drives me to the restaurant where it turns out all his friends are waiting. He leaves me at the table to go play pool with another girl… for the rest of the evening. Then dropped me off at home and tried to kiss me. Seriously?!

  22. I had gone on a few dates with a guy and things seemed to be going well until I visited his apartment. He was showing me around and I noticed a large collage picture frame on the wall. I asked who the people in the pictures were and he responsed: “Oh, each frame has a picture of one of my best friends and his girlfriend or wife. And a picture of me and my Mom.” Seriously too much desperation going on there for me to handle.

  23. I just had a pretty bad date six months ago. the whole time the guy talked about himself and EVERY single truck he owned. THen everytime I would say anything about myself, he would say “OH yea that happened to me…..” and on and on
    WHen I got home, he texted me saying he had a great time. I was thinking, what date was he on? haha

  24. These stories are hilarious! One time (right after college, I was probably 22), I met up with a guy from Match.com for a date. In his picture, he looked like he was in his early 20’s, very attractive, abs, etc. Well I show up, and this guy looked like he was in his late 30’s, had a big beer belly, beard stubble, and rough hands and weathered skin from working outdoor construction for years. Then, as we talked, I found out that he had THREE kids, the oldest being 12. I was like, uhhh, what? Needless to say, I ended the date quickly and never talked to him again!

  25. This is the funniest thread ever! In college, I met a guy at a bar…had a fun conversation, agreed to go out with him. When he showed up, he barely cleared my belly button (nothing against short guys, but I’m tall and this was just too lopsided–I should have waited until he hopped off the bar stool before agreeing to a date). To make matters worse, I was wearing high heels. Anyway, we walked to his “car” only to find it was a motorcycle–and me in a skirt and heels. I get on, we go to a nice restaurant, when we get ready to leave, he puts a single dollar bill on the table for a tip. I was working as a waitress and was totally mortified. I let him go first, reach into my purse and throw a pile of bills on top of his dollar but I knocked a glass of water over in my haste. He turns, sees the money. Awkward. The worst part was, on the way home, he runs out of gas on a stretch of freeway in LA where there is nothing. We had to use one of those emergency phones (which connect only to police) and wait an hour for the cops to help us out. And me in a skirt and heels on a cold LA night with no one i wanted to hug to keep warm.

  26. Just stumbled upon your website and as most of these experiances I have had myself the most crazy was a guy I met at a club (shoulda been a hint) asked me out and he came and got me, we went to some burger place (not first date material) on the way home he got pulled over and ended up being drunk! (we didnt drink so this had to be before he came and got me) and got a DUI and taken to jail. The car was his so I couldnt drive it, in the state I was in it was illegal to ride in a cop car unless in custody so I stood on the side of the interstate untill my friend came and got me! (I was in a skirt) he then called me several times saying that he had no idea how that happened! Pretty sure it was you drinking!

  27. I have a Stefan story too (but that’s for another time)! But the worst date started even before I went on the date… I met him on Match and we exchanged the obligatory couple of intro emails. Then he wrote to me to say that I shouldn’t be afraid of him (ok…who does that?) and that what he was about to write something that shouldn’t stop me from going out with him. He wrote that he knew where I worked and saw me everyday because he worked as a guard at my building and looked me up in their database. SO awkward – should have been an automatic no.

    Anyways ended up going on date. He brought me a huge bouquet of flowers but hadn’t planned where we were going to eat. The poor guy, he was divorced and told me his long sob story about his failed marriage and how he moved back to DC after living in Hawaii. He told me how he didn’t have any friends and that he was struggling to keep his finances up. He kept talking and I kept quiet, just listening. I felt more like a confessional or older sister. He was totally clueless and actually, very innocent and acted more like he was 18 rather than a 29 year old. It was just plain awkward.

  28. Oh I’m so glad I’m not the only one whose had a bad date! After reading through everyone else’s I’m not sure if this qualifies, but I asked out another grad student in my department. I am already a shy/awkward person (and the only first date I had been on was years ago when I was 17, which turned into a 5+ relationship).

    Nothing was wrong with him, but we were clearly not made for each other and very shy and uncomfortable. The waiter couldn’t help but grin at us as he could clearly tell an awkward first date was going on. To make matters worse, we saw some mutual classmates after our date who could tell what was going on and we got more smirks.

    We decided it was not going to work, but since we’re both students in the same dept and have some mutual friends, I still run into him from time to time and it’s just awfully awkward. It would be one thing if I never had to see him again, but when I run into him it’s like the bad date that won’t end!

  29. I could write a book on horrid dates! LOL I’m too nice is the problem. I can’t hurt anyone. I end up saying yes to guys I know I won’t even like and then trying to nicely get out of it.

    Let’s see, we have the 1 that I had my P.I. cousin investigate but unfortunately he called b4 I got the news that he was a convicted and registered sex offender (yeah, that was scary). I always had my cousin investigate EVERY man I ever went out with but this one I met at a restaurant on a whim when he called & said he was there. Learned my lesson there. Nothing bad happened THANK GOD but it was scary.

    Then of course there was the guy that I met that I later found out was homeless. LOL Don’t even ask.

    We have the “I never bathe unless it’s a full moon” guy that I actually within under 30 seconds excused myself to the bathroom & ran out!

    Oh I could go on!!!!! LOL Let’s just say I’m sooooo happy I found my love. I’m with him and happy to be with someone who not only bathes & isn’t registered as any offender but he’s sweet & loving too! He’s truly my knight in shining armor! (Most of the time LOL)

  30. This is not really a disaster but it is quite funny. A guy told me half way through dinner that he didn’t have balls! I know I shouldn’t think it’s funny that a guy lost his testicles but he seemed quite relaxed about it. At least he had the balls to tell me before I found out myself. 😉

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