Day 11: Describe Your Worst/Funniest/Most Embarrassing Date

Day 11My worst/funniest/most embarrassing date.

I could fill pages and pages with horror stories (HA!)….but then again, what single woman in her 30’s couldn’t? Or for that matter, what single man in HIS 30’s couldn’t? This whole dating thing, of spending awkward periods of time over dinner or coffee making small talk with a complete stranger and hoping a spark lights (or sometimes hoping a fire burns the place down so you can escape as quickly as possible) is an odd ritual, at best. Finding two people on the same page at the same time with the same feelings seems as impossible to me as finding a needle in a haystack. Or Miley Cyrus with clothes on. So when it DOES happen…I believe it’s purely magical, and meant to be. I also believe and hope it will happen for me someday. Which makes the awkward coffee dates and endless small talks over dinner completely worth it, because there is no frog in the world I wouldn’t endure an hour or two of misery with in order to finally, finally find my Prince Charming.

Now…that said…I have certainly seen my parade of frogs. There was the guy who asked me for $40 at the end of an otherwise perfectly normal date (the full story is in my book The Single Woman: Life, Love, & a Dash of Sass); there’s the guy who treated our coffee date like a therapy session and within the first five minutes, I knew that his ex had left him at the altar and why; and most recently, there was Rejection Guy. He was probably the most heinous of the Parade of Frogs, as he literally wore rejection on his sleeve. This was about three months ago when I agreed to go out on a blind date with a friend of my cousin’s. Since then, I have established a new rule: The first time I meet a guy, it will ONLY be over coffee from here on out. Never again will I subject myself to hours of misery over dinner or even lunch. I firmly believe it’s best to keep the first meeting short and sweet, and then if it goes great, you can always set up another date. That’s a much better option than fighting to keep yourself from jabbing the steak knife repeatedly into your eyeball just to make it stop.

Anyway…Rejection Guy told me within the first 20 minutes of meeting him that he had been fired from almost every job he’d ever had because his bosses hated him, his roommate hates him, and every girl he’d ever dated was a witch with a “B.” Yes, he actually used that term. Over dinner. With a girl. On a first date. Obviously I wasn’t exactly seeing rainbows and shooting stars.  More like landfills and litter boxes. It was AWFUL. (Not to mention he ate only the centers out of the bread slices the waiter brought us to share, leaving the rinds, which was just plain weird. And left a trail of crumbs across the table long and thick enough to entice every ant in the middle Tennessee area.)

As miserable as the evening was, it taught me a valuable lesson. Carrying around rejection is literally like walking around carrying an open, smelly bag of garbage. It’s unattractive, it’s off-putting, and it permeates everything around you until no one can stand to be anywhere near you. We’ve all been rejected. We’re all at least a little afraid of rejection. But choosing to tightly clench hands with that spirit of rejection and make it your lifelong companion will keep you from ever finding an actual companion. Who knows if I would have been attracted to this guy or would have wanted to spend more time with him had he not carried around his rejection like a badge of honor…but now I’ll never know. And I guarantee you no one else will know, either, until he is willing to make some drastic changes. I feel for him, I do. I know the sting of rejection. But at a certain point, you have to  stop blaming the world around you for your misery and start looking within to see what you can do differently. Most of the time it’s as simple as just lying down the blame and the shame and taking responsibility for your own actions and feelings and choices. By continuing to point the finger at everyone else for every little hurt and heartbreak and denial you’ve received in life, you continue to invite more rejection into your life.

Also, remember that rejection can actually be your FRIEND, if you learn to accept it, learn from it, then let it go. Very often in my life, a rejection has pointed me away from something mediocre or good and toward something GREAT.

Here’s hoping that every bad, miserable, uncomfortable first date is pointing me toward my amazing, spectacular, hand-picked by God mate! 🙂

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33 Responses to “ Day 11: Describe Your Worst/Funniest/Most Embarrassing Date ”

  1. Lisa Qwatekane
    October 18, 2013

    Worst most embarrasing an old relationship frm college tht never realy ended nor started recently contacted me via social media after 8yrs or more an I couldn see him soba minded so I drank an he came ova my place,we slept together an the next day posted a tweet”a mans job is 2 respect a woman but a womans job is 2 give him something 2 respect”offended ofcoz I am bcz I’ve made myslf look like a easy somethin an it hurts coz I’ve not been sexual nor in a relationship for 2 years plus…if I could reverse the night I would

  2. Missy
    October 18, 2013

    My first and only date with this man started at an all you can Chinese buffett. He sweetly said, go to the buffett and I’ll watch your purse. I told him I could I juat take it with me but he made a big deal out of it, so I left it with him only to glance over to see my purse on an empty seat and him in line filling his plate. The whole time, he talked about himself and his accomplishments, the only time he ever asked me anything was when he wanted to know about an ex of mine that he was in the lodge with. After dinner, we went to the movies and he asked me to pick it out. I picked out the movie, he didn’t want to see it, so we went to a scary movie he had wanted to see and I sat in the theater with my eyes closed for most of it. On the way home, we passed some law enforcement officers and the last of our date was spent by him talking negatively about all law enforcement. When he dropped me off, he asked if he could see me again, and I nicely told him no. When I went inside, I immediately called my law enforcement daddy and we had a good laugh about the whole ordeal.

  3. Julia
    October 18, 2013

    My worst/funniest/most embarrassing date hahaha uhh…the date that never was. I surrendered my “I can pick a boyfriend card” and a friend of mine set me up on this date with her cousin named Michael. We talked for a couple of hours over coffee and I thought “Why the heck not”. Sooo…on Tuesday he calls to confirm the Friday date. I confirmed. Then he calls Wednesday to say that I can’t date anyone else because he is my boyfriend now (despite not having been on ONE date yet). I laughed and inquired as to how he came to that conclusion (I still will never stomach or handle well being told what to do). He said that because I agreed to a date that meant we were in a relationship and that I couldn’t date anyone else without asking him first. RED FLAG! RED FLAG! To which lead to me cancelling Friday’s date and hanging up. Thursday rolls around and he calls back apologizing about yesterday and explaining himself. I didn’t care because the guy, while sweet in person, has managed to creep AND freak me out in all of 30 minutes. I hang up again. Friday morning rolls around and he calls to say “WHY CANT YOU JUST LET ME TAKE YOU OUT?!” to which I replied, “with how crazy you are acting, you might actualy take me out with a damn bullet. Don’t call, Don’t write. Don’t email. Don’t text. One more call and I will hunt you down and I wont be alone and God help you then.” So…that was the worst date that never was LOL

    Actual date wise…there was the guy that just kept saying “Let me love you” and wanted to marry me because he knew I was “THE ONE”. But first, he wanted me to co-sign for a jetski. LOL Then there was the man that had the “dog” thing. He brought his dog on a date and I didnt mind that at all. We watched movies at his place and sat his dog on the other side of him and talked to her during the movie (I’ve seen stranger things). When I get the most amazing kiss goodnight as he drops me off…and I turn to unlock the door he asked me (HE WAS DEAD SERIOUS) “Where’s Hannah’s kiss? hahahaha soo…yup! I had a few funnies…doozies…and some other ones I won’t mention because I’m still trying to repress that memory hahahaha 😛

  4. Sarah
    October 18, 2013

    Oh Boy, do I have some funny ones. There was the guy who lived in a camper. The camper that sits on the back of a truck bed. I couldn’t even imagine saying yes to coming over and watching a movie at his place!? Are you serious? Ugh….then there was the ricko suave guy. Kid you not. The guy had his shirt buttoned down to his navel wearing gold chains. talked up a storm about himself. Gross. I don’t even think I tasted my food over lunch. I just swallowed whole and high tailed it out of there. He wanted to see me again and I said no thank you. A real winner was a guy I dated a few times. He was nice and I wasn’t getting any red flags. Well, we then had a date and he proceeded to tell me he wasn’t over his ex. OK, that’s fine. I appreciate the honesty. I let it go and we said goodbye maturely. Well, a few days later he called to ask me where was he suppose to go when he got lonely? AHHH WHAT?!! I hung up. 🙂 Great post, this was fun.

  5. Sara
    October 18, 2013

    Went on a date with a tall handsome R.N. with a psychology Background a couple of years ago. It was the first date I had been on since my divorce from my husband of 12 years. On our date we get talking about what we like and where we are at In life. He started talking about his ex and asked about mine. (I didn’t have much dating experience…I had married my husband when I was young and this was my first date after our divorce). Had I known then what I know now I wouldn’t have gone “there” with him and just changed the subject. Lol. However, I did not. He asked if my ex was involved in my childrens’ lives and I answered “no.” Of course he asked why, so I told him. “He has severe bi-polar and isn’t allowed to see them right now.” He pried further, “Why not?” (I got a little uncomfortable to say the least). I told him my ex husband was abusive, controlling, and unstable. He asked, “how so?” (I was getting a bit irritated at this point and was looking for a way out of this date). I replied, “He has attempted suicide because I won’t take him back and in other ways.” He asked me his name and where he was taken to. Well, anyways…this guy I was on a date with was my ex husbands nurse in the hospital the night he over-dosed. Ugh!!! How embarrassing! He wasn’t upset and wanted to continue seeing me, however, I wasn’t a bit interested.

  6. Amanda
    October 18, 2013

    I went through a period where I thought maybe online dating would be successful. Unfortunately , I was dead wrong. I went on several dates each one was more bizarre than the other BUT the one that really stuck out for me was when I was picked up by this guy who seemed well adjusted. He was going to school and in some kind of salsa band. I’m not really into men who are short and I’m even less inclined to go on a date with a man who is shorter than me. Yet , I found this person wasn’t honest about his height (I’m 5’3 and so was he). That didn’t cut the date short though. He ended up taking me to some Latin bar (even though I had told him in previous chat sessions I didn’t particularly enjoy Spanish music) and then disappeared for about 45min.we were sitting at a table in an empty salsa place and he just excuses himself. I was waiting so long I started texting my mom , wondering if I should just leave. He eventually showed up and explained he had an upset stomach and wasn’t feeling very well. So after I drank my bottle of water, yes a bottle of water was all that was ordered, we left. I was just so dumbfounded I spent nearly 2 hours with this guy and what I got out of it was a bottle of water and some anxiety. He then continued driving and got us lost (even though he had gps) and when he asked if I had a good time and I just gave him a blank look , he offered to take me somewhere else to eat , or take me through a drive thru. Needless to say I couldn’t wait for this date to be over so I refused any extras and when he pulled up to my house to drop me off , he had the audacity to try and KISS ME. Moral of the story eat before you go on a dinner date and make sure you bring your own mode of transportation so at least you aren’t HANGRY or stranded should it not go well.

  7. Denny
    October 18, 2013

    So, I’m black. I go out with a white guy. No biggie, right? Except he spends the entire time talking about why he only dates black women and gives reasons why white women are flawed. I thought of all of my amazing white friends who would join me in a burying him alive while he probably continues to talk. So, I reach for my purse to get my phone to set up the “random phone call so I can get out of this date” text… only to be interrupted by his phone call to which he then had to leave early because his black female roommate was left stranded outside his apartment. Wait, what? Okay… goodbye. Forever. Now that’s the story all about how I got left high and dry by a date I completely hated! haha

  8. October 18, 2013

    Since my date one is also mixed in with my weird behavior post, I’ll repost my link here again.

  9. tia
    October 18, 2013

    NJOYED your day 11 blog.. great!.. got me a chuckling.. but I can’t even remember a date.. really!.. been inna 30 yr marriage just got divorce. and even when I was single. I was too much a good too shoer.. to mess.. and a fool too.. lol… but I am getting better with all the books u listed and UR book too and many others too. I am gonna learn and be more aware.. and get off my naivety horse.. I tell you what.. bye gotta run..

  10. erin
    October 18, 2013

    Well lets see I have had several First Dates that were just awful. On one of them , I was set up with a friend of mines cousin and he was a cop that worked in the birmingham,alabama area.. and we met for dinner at jim n nicks. Litterally, I talked and he listened and just engulfed his food and only smiled like one time at me and went to the bathroom about 5 times .. needless to say we havent spoken since. I have had many many more than that . .but as you said at the end .. i am hoping all these Frogs are leading to my hand picked God mate aka Prince 🙂

  11. Linda Lorraine
    October 18, 2013

    My worst most embarrassing date…. I had meet him online we set up the date for On The Border… we ordered our food, we talked every thing was fine until we started eating. I took a bite of rice and it must have hit the back of my throat wrong cause I started coughing and rice went everywhere. I started laughing. Well he didn’t think it was funny. Needless to say he never talked to me again. LOL

  12. ali
    October 18, 2013

    This guy I knew from school, saw years later and he called me for a date, guy comes, the car is filthy outside and inside, he worked around construction sites, so you get the picture, anyway during the car ride, out comes a cockroach from under my seat, and runs under the dashboard, it mustered all in me not to hop out of that moving car. Needless to say, it didnt work, guy had issues, but if I guy couldnt take the time to clean the car to impress on a first date, then…….

    • Sarah
      October 21, 2013

      I would have DIED. GROSS. You win after readying some of these today. LOL.

  13. Sarah
    October 18, 2013

    An elder couple in my church set me up with their friends son, who was a 28 year old pharmacist following in his fathers footsteps. I was 20 at the time, so I was already skeptical of the age difference. The guy had no Facebook account, so I could only go off of what the couple had told me. We met at the couples home, and went off for a fishing trip at a nearby fish pond. Most awkward hour of my life.. He thought he would teach me to fish, but I already knew how. I even taught him a new knot to use. We had no similarities, I was playing basketball for my college and he knew nothing of sports. BUT – the best part – he……..talked…….so……..slow…….. It was so hard to carry on any conversation because he took 5 minutes to ask a question. He didn’t have a speech impediment, he just had a lonnnnnng southern drawl. To make the date better, my two best friends stalked us in their car and kept driving by, so I couldn’t keep a straight face. He asked me to dinner a little later, and I politely declined. He got my phone number from the sweet old couple, and I never replied. The worst.

  14. Lisa
    October 18, 2013
  15. October 18, 2013

    life is so full of boo boos but i’m sure 5 years from now, we’ll all be looking back at those experiences and we’ll have a good laugh. here’s my worst date story:

  16. Taramgii
    October 19, 2013

    My worst first date was a few months ago. I had met the guy online, we had emailed back and forth every once in awhile for months. I showed up and he was waiting with a rose, I thought wow this guy is sweet! He bought me coffee and we started talking. Well he started talking anyways.. And did not stop talking about himself or his ex wife. I felt more like a councilor then a date.

  17. Ngoni
    October 19, 2013

    Excuse me while I clean the cobwebs in my dating archive. (I haven’t been on a date since ’99) All the men I dated (and I can count them all on one hand) were very nice men. Probably nightmare dates were when my date and I were being followed by some guys in a car because they thought he was gay. Or the time when my date took me to a cafe bar and I threw up later after drinking a cafe latte. Other than that, the dates, (and there weren’t many), were pretty laid back and enjoyable.

  18. Rebecca
    October 20, 2013

    I could go on and on about the numerous bad dates I have ever had. Recently, it wasn’t so much a bad date as a bad 2 week dating experience. I met this guy through my work, and we really hit it off. He said all the right things, wanted to see me as much as he could, then started talking about how his ex fiance (who is still living with him) is moving out in 2 months… That is fine, I get it, she was finishing school and then leaving, I can understand that. But then wants me to move in with him… It has been 2 weeks and you want what?! Needless to say he decided after telling me how badly he wants to come home to me at the end of everyday, he went back to his ex. I look at it now as, what was I thinking? But lesson learned! Men can be pigs and I would much rather find a man that can say all the right things, show me that same affection and put me as a priority.

  19. josephine
    October 20, 2013

    my worst date. ji have had so many od these. allmost all the dates av had were horrible. but this was the worst of them all, I met this guy at the club · I should av followed that advice. Anyway, this guy was all the good things, chubby (i do not like skinny guys) with a nice job, speaks good english (this was very important because at that time i was living in a place wea 2% of the citizens could speak english) So he calls me and asks me if we could meet up for a drink and i was like, “yeah, sure” When we got to the bar, after ordering my first drink, he conveniently tells me how he doesnr have cash on him but he’s going to check his ATM. i was okay with that. only to come back and tell me that the ATM wasnt working! who does that?! u made plans to come take me out and u didnt even come with money?! After that, he boldly asked me if i could spend the night at his place (dude! seriously?! u couldnt even buy me a 2nd drink!!!), i politely said no. he dropped me off to my dorm and before his hands were allover me n thats wen i pushed him away! The next day he texts me saying he’s h***** at work. told him i wasnt in the business of pleasing men and that was the last time i ever heard from him.

  20. […] awkward silences. The whole dog and pony show is ridiculous. I think I’m going to take on Mandy’s rule of coffee first dates only. Even though I don’t drink […]

  21. October 20, 2013

    Umm….I don’t have any. The only guys I dated were back in high school, and there wasn’t anything embarrassing about those dates cause they never took me on one. I’m 29 and haven’t been on an actual date. Is that sad or is it a good thing? lol

    • kathi
      November 24, 2013

      oh my gosh thank God for your comment im in the same boat

  22. Kimi
    October 21, 2013

    The funniest and most memorable would have to be the “ambush date” my closest friends set up between me and the guy I’ve always liked in high school. Around 7 or 8 years have passed, we both had jobs now and were just starting to rekindle the friendship that fizzled out over the years. People have been telling us that we both had feelings for each other, but at the same time, both of us were also too afraid to make the first move—guess we just weren’t ready yet.

    What started out as a harmless planned “get-together lunch” between me and my buddies took a turn for Weirdsville. I took a lunch break from work and met them at a restaurant. Suddenly, something didn’t seem quite right and their bad acting skills gave them away. One pretended to answer a phone call from one of our friends so he stepped out because he said there wasn’t any signal. I looked at my phone and the signal was a full bar. He then gingerly kept on looking at me from the glass walls trying to hold back his laughter and from then on I knew they were all up to something.

    Sure enough, I saw my longtime high school crush outside the restaurant, flabbergasted and having second thoughts whether he should come inside or not. To sum everything up, the date was REALLY, REALLY awkward/painful with me doing most of the talking and him just nodding the entire time. But I guess something good came out from this incident—we’re both really good friends now. At least I could look back at this embarrassing moment and just laugh about it. It’s a memory I’ll cherish forever though. 🙂

  23. Jean
    November 7, 2013

    Like many of the girls on here, some of the worst “dates” in recent times were with dates that never even happened. One was a recent divorcee who worked as a general manager at a chain restaurant. I met him on a dating site, we started texting and calling,  and well, that’s it. He kept making lame excuses to not meet up…yet he still wanted me to devote time to text conversations with him. One day my girl friend and I were planning to take my son out to lunch in the area, so I told him maybe we’d stop by his restaurant and patronize the place. He actually said NO. He made up some excuse about “not mixing work and play” even though there’d been no playing or even meeting yet. What manager would turn away sales?? It wasn’t like I was planning to pull him away from work or anything inappropriate either. Then he kept stalling about meeting me…”whoa, pump the brakes, I like things the way they are.” Did he really expect me to be content with a mere “text message relationship” wtf? Especially when I expressed (both on my dating profile and in text convo) that I was looking for a serious boyfriend that could hopefully lead to marriage? Was he TRYING to waste my time and make a joke out of me? Apparently so. Later he admitted that he wasn’t over his recent ex-wife. “Oh but keep sending me sexy flirty pictures though!” (a big mistake on my part…I started spamming him and a few other guys I was in talk with at the time with sexy photos of myself, in hopes it’d entice at least one of them to actually take me out, since I was striking out and couldn’t even score a hookup, resulting in extreme sexual frustration for me) Ew so apparently his intention WAS just to waste my time. I’d even rather be used for a hookup than that, because at least with a hookup I’d get something out of it.Another lousy date occurred with a narrow minded, high maintenance priss who didn’t like the idea of dating outside his immediate posh center city neighborhood (“I got rid of my car since I live downtown but I do not like taking mass transit”) and couldn’t “navigate” his way to my house from the train station, despite it being only a 10-minute walk and my clear, detailed step-by-step directions. All I wanted was for a man to pick me up at my house for a date the old fashioned way. I’d had numerous friends and dates from outside areas meet me at my house from the train station many times before with no problems. Well he ended up flipping out at me, swearing that this is why he didn’t want to go on a date with a girl like me who lived “so far away” (only half an hour away), and telling me he was turning around and heading back home. I hadn’t even met him yet!!!! Unfortunately, I was already at a rock bottom point in my life at that point and my self esteem was in the gutter, so instead of writing him off as a lost cause douche, I outwardly blamed myself for “having a knack for always screwing things up,” apologized, and went to the train station to meet him. As it turned out, we actually hit it off well that night, at least as friends, but any romantic mood of the night had already been ruined by him blaming me for having him try to go to my house.We did eventually end up going on official dates and I started seeing him, but he soon proved to be one of the biggest jerks I’d ever had the displeasure of dating. He would belittle me in backhanded (and not-so-backhanded) ways, he’d command monogamy from me when he wouldn’t even give me the title of “his girlfriend,” and it turned out that he was only using me as a placeholder until he found something better. Like the last douche, this guy KNEW I wanted a serious relationship but knowingly strung me along and tried to waste my time. I find this to be extremely disrespectful. After this jerk dumped me, he became extremely verbally and emotionally abusive towards me, and tried to literally ruin my life.

  24. Kim
    February 2, 2014

    So far the worst date I have had is when a guy I met on Facebook asked me out. He asked me to come to his town ( which was an hour from where I lived) since there were more options to eat there, I meet him at his house. He then lets me know that his truck is in the shop could we take my vehicle. We go eat and I order a water to be polite and he orders 2 beers and not once said ” you can order something else besides water if you would like”. The conversation at dinner was boring. After I took him back to his house and he asked if I wanted to come in so I accepted thinking we would talk or watch a movie. Nope we watched a marathon on Moonshiners…. I let him know I have to go and he walks me to the door and just starts kissing and grabbing me, I pull away and say bye. As I’m walking to my car he turns off the porch light and shuts the door before I make it to my car. WOW. He texts me while I’m on the hour drive back to my house saying ” he’s going to bed hope U make it home safe” Heck he didn’t even know if I made it to my car because he shut the door and light off before I even got there

  25. Elonia
    April 29, 2015

    ok……so I was really into to dis guy,i went through a lot of craziness just to get him interested only for me to find out he was into me too but was afraid to come close.we started talking,chating and flirting on phone cause we were far away from each other.”oh here comes the most shameful part”he called me and told me,he was in town so i asked him to come around to my house,he did and he got naughty too bad i told him i can’t have sex with him cause i was still on my monthly period.he wouldn’t listen he continued caressing me and dipped his finger into my pussy… comes the foul smell.. i was so embarrassed i pushed him aside and went to wash up but he was still interesting in making love to me on top of my period.i refused and he left,he called once that evening and never called again….I felt bad cause i really wanted him

  26. Debby
    July 22, 2016

    I really liked this guy Liam, and I found out he liked me too. So he called and asked me to come to his dads pizza place and when I got there, his whole Italian family came out singing and dancing saying “we love you he love you!” I was sooo embarrassed!! Even worse, he came out and tried to full on smooch me in front of his ENTIRE family. I pushed away and said I had to go. He called me later that day saying he loved me. I blocked him and changed my cell number! Soo embarrassing!

  27. […] 5. He told me that everyone hated him and that ever girl he ever dated was a bitch. […]

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Something wonderful is on the horizon
Turn Toward the Sun CoverLife doesn’t always look the way we want it to look. In Mandy’s upcoming book, Turn Toward the Sun: Releasing What If and Embracing What Is, you’ll find encouragement to live in the moment, sit with your experiences, and trust God with the unknown.
Preorder from Baker Book House for 40% off and free shipping!*
*US shipping only