Daily Happenings, Dating

Our First (Worst) Date

Hi friends! I have a different post for you guys today that I hope you enjoy. A year ago today is when Alex and I went on our first date. It wasn’t the best date either of us had ever been on. Actually it was probably the worst date, let alone first date, for either of us. We decided to share both sides of it for you today! We hope you find it funny and can laugh at our experience.

P.S We both apologize for how long this post is! Apparently neither of us can shut up 😉

Maureen’s Side

I don’t remember if I’ve ever stated this on the blog before but Alex and I met on Bumble. It’s a dating app that is similar to Tinder. We both “liked” each other’s profile and then the ball was in my court. Honestly, I was kind of over dating at that point and decided I would try one more person and then stop dating for a bit if it didn’t work out. Alex happened to be that last guy (in so many ways). With Bumble, the girl has to message first. I’m pretty sure I started with a lame message along the lines of “Hey! What’s up?” and it could have been exactly that. We talked a bit and I thought he was nice and he ended up asking for my number pretty quickly so I gave it to him.

We were texting and he asks if I wanted to go out that weekend, it was Tuesday at that point. I agreed because by then I would’ve been talking to him more and known if I really wanted to go on a date with him or cancel. Well…someone had other plans. After we agree to that weekend he says that he “forgot” he was going out of town that weekend so could we move the date up. I said sure but I have night classes Thursday so does Friday work. Nope it didn’t because that’s when he was leaving. So it had to be Wednesday. Y’all…not only had I just started talking to him but then I was going on a first date with a guy I barely knew and had started talking to about 24 hours before the date.

I don’t remember what it was but I had something after work that day so was rushed to get ready for the date. My roommate Sarah knew about the date and was helping me decide on my outfit, luckily I did my makeup for the date before work so just had to do minor touch ups. Sarah and I were talking about me potentially changing and then I get a text from Alex saying he was here. Being the good friend she is, Sarah goes and tries to stand at the top of the stairs and stare out the door to see him but without Alex seeing her. I vaguely remember her saying he was cute which was a good sign but I was so nervous!

Now if you haven’t dated in the age of cell phones, it’s a bit different. Boys don’t walk up to the door and ring the doorbell to get you and will opt for just a text saying they are here. I honestly thought that was what he was doing but nope, he came up to the door and got me, which was definitely a plus in my book. I saw his face and thought “He’s cute” then realized he was wearing pink pants. Yes a 22 year old male was wearing pink pants my friends. I found it a little odd but now I know that Alex has a preppy sense of style so colored pants and shorts are the norm. But this was the first date so I didn’t know that at the time. Nervous about pink pants but I put it behind me and we were off. We walked to his car down the street and as he goes to pull out of the spot, I  nicely told him he had a hole in his shirt. I thought he knew but he was clueless! So right there it was off to a good start…

I told Alex he could pick the restaurant but I didn’t eat seafood. Luckily he picked a restaurant I had been to before so I knew I could find something to eat (picky eater problems). As we walk into the restaurant he put his hand on my back and it creeped me out a bit. I thought “Okay I barely know you why are you touching my back” and it was a negative in my book. We get seated and are chatting over our drinks. He asked if I wanted an appetizer and I wondered if he would share fried pickles with me. I don’t know if he agreed to be nice or because he actually wanted fried pickles but we got them. The appetizer comes and we order our food. We’re still talking over beer and fried pickles and I ask him a very simple question: “How many siblings do you have?” His response was “I want four kids.” I almost spit out my beer onto him. It was a first date, why is he telling me how many kids he wants?!?! I was nervous enough and that made me even more nervous. My personality is much more introverted and his is more extroverted so I kind of went into my shell and kept eating the pickles because I figured if my mouth is full he won’t expect me to talk.

That plan back fired because I started to not feel so good. The entrees came and we kept talking and getting to know each other. Honestly, I was ready to go home and put my pjs on but he suggested we get ice cream. I didn’t want to be mean so I agreed even though I didn’t feel that good. He touched my back another time or two and I kept thinking it was kind of weird since we barely knew each other.

It was a warm September night so the line at the ice cream store was long. While we’re waiting Alex turns to me and goes “I don’t think I answered your question earlier, I’m sorry. I want four kids.” So twice on our first date he told me he wanted four kids! I was starting to think he was crazy. We ordered our ice cream and sat down to talk and eat. Keep in mind I didn’t feel that good so I was struggling to eat the ice cream. I didn’t even finish which if you know me in real life is very rare. Afterwards, he drops me off at the front door and gave me a kiss goodnight.

Of course Sarah wanted to know how it went and I told her a little bit. I don’t think I said it was awful but I don’t remember if I said it was great either. He texted me when he got home and said he told his parents about me. Again, I thought that was kind of weird but I guess it isn’t if you live at home with your parents lol. Can you tell that made it obvious I went to a college 800 miles away from my parents, they didn’t even know I went on a date. Anyways, we kept talking that night. To this day, I don’t know what it is that made me keep talking to him but his charm did something to me that night to make me want to keep talking to someone who told me multiple times (and still tells me) he wants four kids.

This isn’t the first date but the next morning I asked him if he really told me how many kids he wanted because I didn’t believe it really happened. Alex thought I was asking him and said “4” for the third time. And the next day, I literally sent him a text listing 6 or 7 things he did or said that bothered me. Looking back that should’ve made him run but somehow it didn’t. We laugh now but I think we were both a little embarrassed about our first date. At least it’s a good story! I will say that having such a bad first date (and picking his drunk dad up on the second and his twin sister apologizing for “ruining” our third date) really set us up for a strong relationship. I couldn’t love him more and yet everyday I do.

Alex’s Side

Maureen real quick – I have not read Alex’s version of the story! He wouldn’t let me so when this post goes live it will be the first time I see it.

For our one year anniversary of meeting, Maureen has asked me to write my side of our first date. Knowing Maureen, her version is going to resonate quite well with any girl that’s ever been on a bad first date (don’t lie, you’ve all had ‘em), but I didn’t come here to go down without a fight! I’m here to represent the underdog in the dating world; the maltreated, misrepresented, forgotten man in this game of love: men! (e.g. me in this situation) I know there are probably few (if any) men reading this, so I’m at a strategic disadvantage, but I’m asking you ladies to hear me out.

I match with Maureen on Bumble and manage to get a response. That in itself is quite an achievement, trust me. So I start working my magic (i.e. asking her the most basic questions I can think of to keep her talking to me) until I can find an opening to ask her out. I ask her if she’s free that weekend for dinner or drinks; I get a big fat “I don’t know, I have to check my schedule. I’m really busy.” Strike one. I try some other options that week (nope, she has classes apparently), so I try a new tact!

I start asking her what kind of food she likes, which if you know Maureen is essentially nothing. “So you basically don’t eat anything?” I ask after hours of trial and error (mostly error). Her response to my question? “Yeah, I’m actually an alien. I don’t need food to survive.”

What? Are you kidding me!? What am I supposed to say to that? How do you respond to someone, especially someone you’ve never met, that’s avoiding a date with you by telling you they’re a flipping alien? I wasn’t about to become a quitter though, so I persist. (Shooters shoot, am I right?)

I eventually convince her to go on a date with me that weekend. Great, we have a plan in place, we’re having dinner on Saturday. Unfortunately God works in mysterious ways and decided to interfere, i.e. by reminding me that I was supposed to drive to Syracuse that weekend. Rats, need to reschedule.

With a fair amount of arm twisting and maneuvering I convince her to move our schedule up and meet me the very next night for dinner (I know, I’m a heck of a salesman). Awesome, we made it! Now the hard part: Where do you take someone, that won’t eat anything, on a dinner date, in a city you know absolutely nothing about? Not an easy feat, I assure you. After hours of searching for the best restaurants I can find in New Brunswick (quite a limited selection) I finally find one that serves something she’ll eat – fried pickles. Alright, I can live with that.

I rush home from work, shower, throw on my favorite clothes, and leave to pick her up, excited and ready to turn my ‘A’ game on for this cute girl I’m trying to woo. How does she start our date off? She gets in the car; we start driving; we make it one God damn block, and she turns to me and says “Um, I’m not sure if anyone’s told you this, but you are aware that you have a hole in your shirt, right?”

I’ve clearly miscalculated my adversary here. This is a huge mistake.

Alright Alex, not a huge deal. You can sell ice to an Eskimo, you can most certainly get around faulty laundry! We make it to the restaurant and it starts out fine. She’s laughing here and there, the drinks are good, the fried pickles actually weren’t that bad (little did I know we’d be buying them any chance we got every single time we went out). So dinner rolls around and we start talking about our families; now we’re in for some real trouble.

I don’t know if it was the beer, the noise, or years of playing in concerts with no ear buds, but one misheard question derailed our entire evening. I swear, this simple question and answer exercise couldn’t have gone more awry if it were on a sitcom. What is this question I’m referring to, you ask? Well, what Maureen actually asked me is “How many siblings do you have?” A fairly standard question for a first date, right? Apparently not, because that’s not even close to the question that I heard!

What did I hear? What I (quite unfortunately) heard was “How many kids do you want to have?”

(How many siblings do you have? How many kids do you want to have? I mean, when you put it in context (re: beer, lots of noise in the restaurant, and slow but steady hearing loss from years of touring), the two can get mixed up quite easily. Anyways, back to the story!)

Well jeez, that’s a lot more intense than I expected this date getting. But like I said, I’m no quitter, shooters shoot! So I tell her exactly what I had planned (like her, I’m a planner). “I don’t know, I think I’d like to have four kids. I feel like that’s the magic number.” Her response? To quite literally eat everything in sight! I’m not kidding, I’m pretty sure she mumbled some inaudible response, and then proceeded to stuff her face with the entrée and fried pickles as if she were a malnourished hitchhiker that just discovered the remnants of the Cheesecake Factory’s unsold Saturday dessert menu.

So I did what any guy failing on a first date would do, press onward! I proceeded to talk about where I want to live, where I see myself in five years, and laid out the twenty year plan. How did that pan out for me? Not too well I’m afraid; the date spiraled downward faster than Lindsey Lohan’s post Mean Girls career.

After another half hour of conversation that went almost nowhere (which was entirely my fault), I suggested dessert. Much to her dismay, we ended up going across town to get ice cream. Little did I know, but she was so full from trying to block out my ‘20 year plan’ rant that she had absolutely no room for dessert. So how did I proceed with this (unbeknownst to me) botched date? By being a perfect gentleman and finishing her ice cream for her of course.

By the time I got her home she couldn’t have run up the front steps fast enough! (Granted, I’d probably run up the steps and deadbolt the door in her shoes, but unfortunately I don’t fit in a size six.) I just narrowly managed to get a goodnight kiss and headed home for the evening. What followed is hardly the making of a blossoming relationship.

Our conversation the next day ended in me pestering her about the date that didn’t go well (which I just couldn’t understand why), and then the cherry on the cake! She sent me a numbered list (no really, numbered 1 through 6) of things she disliked about me and our first date. I’m not kidding! She quite literally wrote out a numbered list of all the things she disliked about me and our first date (while she was at work, mind you) on a notecard and sent me a picture of it the next day. Now if that’s not extra, I don’t know what is! And yet our story continues….

So you might be wondering, how did I respond? Quite simple really: I asked her on a second date, which (spoiler alert), went totally sideways! (The story involves Alabama football, puppies, drunken family members, Uber’s newest taxi service rival (re: Alex & Maureen), and heavy alcohol consumption in a pool house belonging to a friend from our country club). But that’s a story for another time.

And where are we now? I’m still working on that numbered list of things she was upset with me about, and she’s still grappling with the prospect of raising four kids, so I’d say we’re pretty even. Until next time!



I hope you all enjoyed our sides of the story! Thank you so much for stopping by today. Again, we apologize for such a long post!

Question of the day: Do you have a bad date story? Alex Here: Not a chance in creation that it’s worse than ours.

20 thoughts on “Our First (Worst) Date”

    1. That’s so funny! I think it helped we both agreed that the first date was awful and to give it another try. We basically went from a terrible first date to hanging out all the time and just got along so well!


  1. Lol, that is amazing!!!!! Glad you guys were able to see the humor in it and obviously have had better dates since. I’d love to hear how you got from the first date to now. I went on a date with a guy that a friend set me up with shortly after college, he asked me at least 18 times if I was actually single. It was very uncomfortable and we did not go out again.


    1. I’m glad we saw past it too 🙂 Maybe we’ll write a follow up post on how we went from the worst first date to planning on marrying each other.
      That is such an uncomfortable date, I wouldn’t have gone out with him again either. Why would you go on a date if you weren’t actually single?! Makes no sense haha.

      Have a great day girl!


  2. Pingback: Knoxville Day 1

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