Dating Disasters

Mastermind Weekend 1/16

Hey there!

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.


An in-depth, 4-week reverse dieting course for women who feel like their metabolism has slowed down, think they might have hormonal imbalance and can’t lose weight no matter what they do.

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?



  1. Wow! Here’s mine. It happened in high school. I went out this guy Nick a few times but I wasn’t in to him. So I called it quits. We literally had gone to the movies twice…c’mon we were 16…we’re not talking major dating going on here. Well he was so upset that he called the radio station (the most popular one that everyone in school listened to) and got through. He told the DJ he was upset I had broken up with him so what did the DJ do…um…they called me ON AIR! Thankfully I wasn’t home but my answering machine picked up (I had my own phone line) and the DJ left me the message about how I should give Nick another chance. The next day at school everyone (and I mean everyone) knew about it and teased us for months. I never did give him another chance.

  2. My only thing is that I met some real weirdo’s through online dating. I went through a few of those before I met my husband. 🙂

  3. Hahahaha that is definitely a funny story. My best one comes from my senior year of high school, when I agreed to go with one of my friends’ friends to his prom because his date had bailed on him a few days before. He ended up being a total creeper, and in order to turn him off I rambled about how much I love the Titanic the entire hour-long limo drive home. It worked…and he ended up going after a 14-year-old at the afterparty. Creeper, I told you.

  4. Mine would actually probably be my first date ever in 8th grade (I guess I’m lucky – I don’t have any other horror stories!). For some reason I decided to bring my 3 best friends with me and have one of their moms drive all 5 of us in her minivan to the movies. It was around Christmas time and one of my friends had some mistletoe so she started dangling it over our heads in the van. I got annoyed so I flicked it away, in the process scratching my friend’s eye. Nice. Well, she was ok, and the date was ok from there, but we didn’t last too long in the romance category. Ah, young love!

  5. Wow Tina, I have a similar story. In freshman year of collegfe me ad my roommate met this group of guys the first night there. We hung out with them a lot of the weekends, they were perfectly nice. It was clear one of them hasd an interest in me and I had zero interest in return. He wasn’t my type and some of the comments he used to hit on me were a turn off. One night he called me 38 times. We finally made up the excuse that I was in the library studying and he went there to find me. Creepy. When he realized I wasn’t there he attempted to get into our dorm. My roommate had to deal with him and needless to say we didn’t hang out when them again. Maybe they weren’t perfectly nice guys afterall!

  6. oh man, this guy took me on a date then we went back to his dorm (it was my freshman year in college) and we hadn’t even started the movie and he was already trying to make out with me. guess he thought i was more into the date than i was…and i guess that means i was a pretty good actress 😉

  7. Wow! That is an awful date! I don’t blame you for getting away as quickly as you could! In the past, I went on so many bad dates I don’t even think I could keep track of them.

  8. What a kook!! I wonder if he knows why you never called him back.
    Anyway, no dating disasters here. I’ve been married to my high school sweetheart (and only boyfriend) for almost 20 years. Did we ever have date disasters? Yes, like the time I was suppose to be back home at 10 pm (I was 17) and the car wouldn’t start!! We were totally panicked!

    Hey, do you cook the bulgur before you put it in the oatmeal?

  9. Met a guy at a club (bad start). Talked all night until the club closed – 3am in New York – then for another half an hour in the parking lot, and no shenanigans! He was so sweet, scuffing his feet on the ground while asking if he could call me, then kissed me on the cheek goodnight.

    Next morning I go out to breakfast with girlfriends and am seated next to a table where…he is having breakfast with his girlfriend. Being the mature adult I am I introduced myself to her and said I couldn’t wait to get his call.

  10. If you’re the queen of bad dates, I’m the queen of boring dates! I tend to find a lot of guys who I leave a coffee / dinner / drink / movie etc feeling “meh.”

    Although my best bad date was coffee with a guy I’d met online. He spent the entire time going on and on about himself. Each time I would try to participate in the convo (ie. Oh you like that band? I saw them live…) He would appear annoyed that he’d been interupted. At times he would even look out the window while droning on. There was no pause in the convo and I was new to dating at the time and felt rude about just interrupting him to walk out. I was trapped there for almost 3 hrs!

    The me of today would have stood up after 20 min and said see-ya!

  11. Oh man, I have too many!! I think most of them are hilarious in retrospect though. Without so many dating disasters, life would not be nearly as entertaining! All part of the joy of being a young singleton :).

  12. When I hear stories like that, I cringe! It makes me happy that I’ve been with my fiance for 8 years and that we are about to tie the knot!

  13. hahaha oh my gosh that story is terrible. It is one thing for him to get drunk but then the calling/texting thing is crazyyy.
    My junior year of high school I went on a date with a really cute senior at my school. It went well until he suggested his romantic fantasy to me – dancing with no music under the stars. I kind of laughed but he asked if I wanted to try it. I was too nice to say no so we drove to an empty parking lot, got out of the car, and started to slow dance with no music. It was our first date-who does that?! I eventually told him it was weird & he took me home. When I was avoiding his calls/e-mails over the next couple weeks he repeatedly mentioned the romantic dancing.

  14. Hahaha that’s a great one! I don’t have any horrific stories, but I’ve received some rather amusing drunk texts. The senders didn’t last very long! 🙂

  15. This isn’t my worst dating story, but it’s kind of funny. In 9th grade I was “dating” (I say “dating” bc in 9th grade, dating was talking on the phone still) this boy who was a year younger than me. I was so “in love” and then he called me from basketball camp (with his friends laughing in the background) and kept repeating, “Would you cry if I broke up with you?” over and over again. I kept saying, “No, just do it then.” And then finally he said, “Then start crying!” and hung up. Eeek. Not the best..he called after he got back from camp to try to get me back but I said no. We are actually really good friends now and he still is so embarassed by that.

  16. I was on a date once and the guy told me that he had to buy extra large underwear because his “thing” was so big!

  17. ewww! i had my first date on years ago when it was first starting. i met this guy online and it seemed like were were destined to be together 🙂

    i had him pick me up at my house (DUMB) and when he showed up, he was literally, at least 7 inches shorter than he said he was in his profile. now, i don’t care at all about height, but i DO care about lying. so, anyway, we went out to dinner and all he could talk about were the great backrubs that he gave (CREEEEPY!) and he tried to convince me to let him give me one when he dropped me off. i can’t believe i stayed on after that, but i did.

  18. Classic!! That story is hysterical. I have a similar one…my gym crush (guy I did not know, but was always at the gym at the same time as me for years) finally asked me out on Valentine’s Day while we were at the water fountain. Sweet start, huh? We went out once or twice and he seemed ok. Then one night he got wasted with his friends on a weeknight and called me up at 9 pm, asking me to come over. I was like, uh, no, I don’t think so. Then he proceeded to call me a gold digger (and sing the song!!) because he thought I only wanted to go out on dates and to dinner!! And I had paid for our last date, actually! He tried to apologize and even sent me flowers after the fact, but I couldn’t get past his craziness…

    Dating stories are such great entertainment. I want to hear the Stefan story now!!

  19. First off, I didn’t even know I was going on a date. I was in the student government in college and one night we had a late meeting and I was showing my colleagues my new fake ID when one of them suggested we try it out on Thursday night. He said we should all go to a local pub together and see if I could get in. When Thursday rolled around he called me to change plans and tell me “they” were all going to a Mexican restaurant in town for the margaritas. When he came by my apartment to walk me over there he was alone and I quickly realized that we were the only two going to the restaurant. Once we got to the restaurant (after a very long, cold walk) he proceeded to order tons of expensive pitchers of margaritas along with his dinner, make remarks about what a nice “date” we were having and then demanded we split the bill 50/50 (some date!) even though he ordered WAY more than me. On the way home we were slipping and sliding thanks to a storm that had covered the sidewalks in thick sheets of ice, so I pleaded with him to grab a cab. He told me he didn’t have money for a cab, so I said no problem I would pay but I couldn’t walk any further. He refused to let me get a cab because a “lady shouldn’t pay” but still refused to pay for one because of his finances. It was the longest, coldest and most awkward 20 block walk home because I was FURIOUS with him. Needless to say I never went out with him again and reevaluated our friendship.

  20. i’ve had many, many bad dates, like the time a guy insisted we go out on valentine’s day and had me pay. but i think one of my favorites was when a guy bought me “yoga for weight loss.” i’m 5’2″ and 108 lbs…

  21. LOL hilarious! I actually didn’t date very much at all. I always ended up dating someone who had been my friend for awhile…and I’ve been in 3 serious relationships lasting 3 years a piece….and I”m 23! How crazy does that sound? I’m a serial monogamist, I guess!

  22. I’ve been on lots of first dates. Overall, they aren’t horrible but some of the guys do/say ridiculous things. I met this guy “Mike” online. He seemed nice enough so we met up for drinks. He was super attracted, Austrian, and very smart. Everything was going well until about 30 minutes into the date. At that point Mike informed me that he liked me a lot, but he had to let me know this dating rule he has. He told me that if he doesn’t sleep with a woman by the 2nd date he doesn’t go out with her again. He claimed that he felt women used sex as a way to get free dinners, gifts, etc so he liked to make sure a woman really liked him and wasn’t using him for those things. I was floored. The best part was he got up a few minutes later to go to the bathroom and both the bartender and the guy next to me said to me I can’t believe he said that. I made sure I paid for my own drinks that night. While I appreciate honesty, it has been the most ridiculous thing any man has ever said to me.

  23. That is too funny (and it would bug me out too)! My worse dating experience occurred my freshman year – I was so naive. Essentially we dated for 3 weeks, and then I broke up with him because for only dating 3 weeks, he did some crazy things – gave me a poem and told me he wrote it when he had clearly plagerized, he stole flowers from the dining hall and gave them to me (my roommate at the time was appalled because she recognized the flowers), among a whole host of weird things. After we “broke up,” I was talking to some mutual friends and found out that he had told people all these ridiculous things about me – I was and still am a goody goody. I was FURIOUS. I was so annoyed with him at that point. I didn’t even want to be friends, so I ignored him (my go to tactic for creepy boys). To this day, if I run into him, I walk away…UGH!

  24. I love reading all these! I just started dating again and met a guy who told me about his internet porn addiction on the first date! I did not go out with him again.

  25. Ugh. Where would I start? Pretty much my whole dating career was a series of bad dates. The worst, however, was freshman year of college. I had a crush on this guy we’ll call Tony. Finally, around Valentine’s, I get the courage to ask him for a date. He takes me out to the happening spot for Valentine’s and at the end of the night, oh-so-casually tells me he has to pick his girlfriend up from work now so he has to cut the night short. Waah??

    Well, then, he ends up telling his flatmate about me, then his flatmate, Matt, asks me out. Thinking it couldn’t get worse than Tony’s scene, I agree.

    Matt picks me up for a date an hour before reservations at a local restaurant (he was trying hard) and wanted to bring me to meet his parents. On the way to his parents house, he was telling me about his parents timeshare in Aruba (or some other island) and how he’d love to bring me that summer and then adds the detail that there are tons of topless beaches. I should have cut the date early at that point. But, I didn’t. It just got worse and worse from there. Ugh.

    How I ended up with my awesome boyfriend out of this is beyond me with my dating record.

  26. Through mutual friends, I had met a guy that kind ran on the outside of my social circle in college. We started chatting over e-mail and IM and he asked me out. I agreed and we were to meet at a local restaurant. I get there, and I see him, sitting at a booth, chatting to one of my friends. I thought, “Oh! Crazy, he must have ran into her here.”

    I walk up, we go through a bunch of “What are you doing here? It’s so nice to see you!” stuff and I expect my friend to leave. When she doesn’t we start to realize something is up. Turns out, he had invited us BOTH out on a date. At the same restaurant. At the same time. He said something like, “Oh, I thought you two would be cool with it!”

    We asked him to leave and my friend and I had dinner together. 😛

  27. Wow, that is awful. I have to say that I haven’t had too many bad dates since I started dating my husband when I was 18! Almost 11 years later, I can’t say we’ve ever had a truly bad date 🙂 I do remember every detail of my first date with him though (which was fantastic) 🙂

  28. I went out with a guy from Match a few months ago. We’d texted and had a few phone conversations for a month or so before we met in person (we weren’t in the same town). He was really nice, but it was really obvious that he was looking for something MUCH more serious than I am at the moment. So I called him the next night to let him know that, while I had a good time, I didn’t think we were looking for the same things. He started CRYING! Half of me wanted to say “Grow a pair!” and the other half felt like I kicked a puppy.

  29. A friend set me up with a guy she professed to know “really” well. He insisted on picking me up, which seemed chivalrous at the time. As we’re walking to his car, he says “there’s something I should tell you. I’m a recovering alcoholic.” Okay, no problem. Then he continues, “so my car is equipped with a breathalyzer.” Umm. What? Yes, he actually had to blow into a tube to start the car, then he had to repeatedly blow into it while driving to keep the car running. Why oh why did he offer to pick me up?!

  30. I once dated this guy that would CONSTANTLY text me with stuff like “you’re a princess” and a ton of other really mushy stuff. It was alright at first, but then it got insane. We went on a few dates and had absolutely nothing in common. We literally sat there in complete silence, yet he still chose to text me every chance he got. Until one day he wrote me a FOUR page text saying how I was his world and all that. I promptly wrote back saying we don’t know each other nearly well enough to talk like that. And the texts stopped. 🙂

    As for the calling thing, my ex’s record was 108 calls and about 20 messages in one day. -_-

    Good thing I finally found a boy that doesn’t make me want to drown my phone.

  31. Blind date. He was coming to my city (about a 20 min drive for him -no biggie) so he asked me to pick a restaurant. We meet outside. He tells me he just passed this really cute place and demands to go there. We arrive at this fabulously expensive little bistro. He then tells me he only has $50 and we’re going to have to split. (Aside: I happen to know that he is quite wealthy and just didn’t prepare to go to a fancy restaurant. No problem except he demanded to go to one.) I ordered soup. He ordered a whole chicken dinner.

    Multiple times during the date he would ask my opinion on something, disagree, and then tell me I’m just a woman so what do I know.

    And then, he asked me where we should send our kids to school and what kind of engagement ring I wanted. HUH? He told me he wasn’t going to let me go. I laughed in his face.

  32. So true..this wasn’t a dating story but more a T story..a guy sitting across from me on the green line was drinking a big dd’s iced coffee one summer when I was coming back from work and he kept trying to talk to me and I just ignored him..he was creeping me out. So he got off at Park Street and threw his empty iced coffee cup with ice across the floor of the train at me and said “you’re cold as ice, baby!” I thought I was going to die of laughter!!

  33. Thank God I didn’t do much dating at all — I have heard too many dating nightmares.

    In high school a boy took me to Toys R Us for our date — he would put the masks on and make strange noises — it was strange!!!

  34. That’s a pretty crazy date. Guys can be so sloppy when they’re drunk.

    Mine was not as crazy, but I was working in the mall for a few months and one of my co-workers who I talked to regularly asked me if I wanted to go out to dinner after work one night. I said yes and we had a pretty fun night. In the middle of our date, I noticed he was calling me nicknames…but avoiding my actual name. I then asked him “Do you even know my name?” He was like Nope! and laughed it off. I thought this was pretty jerky of a guy to do… ask a girl out and not even know her name. I am not proud of going out with him.

  35. I think I have mentally blocked most of my dating disasters. They seemed awful at the time, but I can only remember bits and pieces! One that sticks with me is a date party I went to with a frat guy (I know). We went bowling somewhere in Detroit on a chartered bus. He proceeded to get really drunk and sloppy, pawing at me and then throwing up on the bus. Classy. I ended up hanging out with the girlfriends of some of his frat brothers & we became friends, so I guess the night wasn’t a total loss!

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