Creeper Snacks: An Online Dating Story

I’m forewarning you that this is going to be long, but it’s worth it – I promise.

I’m not new to the online dating world. After getting out of a four-year relationship where I was living in a new city and lost most of my friends with that relationship, I didn’t exactly know where to turn when it came to finding someone. Milwaukee was definitely known for it’s bar scene, but it wasn’t really doing it for me on the compatible male front. I did try to convince myself that the stupid 22-year-old British bartender that I saw every weekend was perfect for me, but that was a no go. The accent blinded my judgement!


So, insert online dating. I’ve tried Match, OK Cupid, Plenty of Fish and even dappled on Tinder for a couple of swipes. I talked to quite a few guys over the last two years, but few have made it to the dating stage (or really, even the messaging back stage – yes I’m one of those mean girls that rarely replies). I’m very closed off when it comes to dating, so it takes someone pretty intriguing to get me out from in front of my protected computer to actually meet someone. It also doesn’t help when your first EVER online date is as crazy as mine was …

His name was Austin and he seemed like a nice guy. I started talking to him on Match about two years ago when I was still living in Milwaukee and I really liked his sarcastic humor. He only had one picture (which is a RED FLAG LADIES), but he had just gotten out of the marines and I was all about that military thing. After chatting back and forth for a few weeks, I finally stopped making excuses and agreed to meet him for coffee in December 2012, right before Christmas. This is where it gets interesting.

Austin told me he was running a bit behind because he had to stop at Target before our date (no judgement there – I’m all about that Target world) so I waited in the parking lot for him at Starbucks. He finally texted me that he was there so I got out of my car and starting walking into the store. All of a sudden I hear, “Jessie – HEY – Jessie!” from behind me. I had walked right past Austin. Want to know why? He looked absolutely NOTHING like his one little photo on Match. Zero percent. He was at least 50 lbs. heavier, was wearing glasses and was dressed in sweat pants and a sweat shirt. No offense to him, but I knew immediately that there was no physical attraction. I awkwardly smiled at him, gave him a hug and then walked into Starbucks, not realizing what was up his sleeve (or really, more like what he was carrying).


He bought me my drink and then we sat down in the back. At that moment, I noticed he had a large Target bag with him that seemed to be filled with things. Before I could start trying to make a conversation, he lifted the bag onto the table and dumped out five individually wrapped gifts and said, “Here – open these.” I was like, “You didn’t have to get me anything!” to which he said, “I wanted to make our first date less awkward, so I decided to bring you some things. Just open them!”



So again, because I suck at making people feel bad, I grabbed one of the gifts and started unwrapping it. The first thing he got me was packaging tape and big markers. Trust me, that seems super creepy, but I was getting ready to move out into a new apartment at the time, so it was actually *slightly* thoughtful (still creepy). The next gift was a box of Oreos. No idea why. The next gift was a family-size box of fruit snacks. Again, where is this coming from? He also got me a package of Dove chocolates (that was actually a smart choice), but I never told him I liked any of those things. He just told me that all girls like food, so he got me those.

The final gift was the kicker – a journal. As I took it out, I noticed that there were photos of England on the front to which he said, “I know you love Ireland and Ireland and England are basically the same, so I knew you’d like this.” UM NO THEY ARE NOT THE SAME YOU MORON. I opened the journal only to find that he had written my first, middle and last name in it (I gave him only my first name, so dude did some creepin’) and a few pages filled with motivational quotes that he thought I would like.

The date can’t get anymore awkward, right?


Again, because Jessie is too busy being nice, I couldn’t figure out how to get out of the date. I mean, he brought me presents! I can’t be like KTHANKSBYE, though I should have. Here are a few things we talked about that go perfectly for a first date.

1) My ex-boyfriend: He asked me if I was over him, why we broke up, if I was a bad girlfriend, etc. Aren’t you NOT supposed to bring up exes on first dates??

2) My minor in college: He could NOT get over the fact that I was a Women & Gender Studies minor. “Oh, so you’re one of those feminists? How come you’re wearing pink, then?” and “So, you think women are equal to men, then, right? I mean, I just don’t know if that’s true.” How he thought he was getting a second date with that, I have no idea.

3) Politics: Sweetie, just no. Let’s not go there ON THE FIRST DATE AFTER YOU JUST GAVE ME FUCKING FRUIT SNACKS YA CREEP.

Finally about an hour in (I know, I made myself go through so much pain just to be nice), he took a phone call (strike number 9 million) and had a 3-minute conversation with his dad. I took that time to text my friend and tell her that she better be ready for an interesting phone call in a few minutes. Once he hung up with his dad, I told him that I thought it was about time I left because I had an early start to work the next day (lies) and his response was, “That’s okay, I’ve gotta go home and take my yum yums.”


So me, being inquisitive and stupid for getting into another conversation with him asked him what a yum yum was, to which he replied, “Oh, my anti-depression medication.” Now, don’t take this in a bad way – I have family on anti-depressants and I’ve been on them as well. No judgement. What I judged is the fact that he calls them YUM YUMS.

I’ve never gotten out of a chair so fast in my life.


I’m not done yet.

As we walked to the door, he grabbed my bag of gifts (I was trying to forget them…) and trailed behind me, asking when our next date would be. I ignored him, but held the door for him. Right as we walked out the door, he points at a sign on the door that says guns aren’t allowed on the premises, “Oh, good thing they didn’t check me! I’ve been packin’ the entire time.”



I calmly asked him why he had a gun on him (lies, I probably looked like I was going to puke) and he said, “Well, there’s been a lot of shootings lately. I just wanted to be able to keep you and me safe.”


I headed straight for my car (casually walking running as fast as possible), grabbed the gifts from him that he insisted I take and peeled out of that parking lot like you wouldn’t believe. I took the long way home, called my girl friend and slept with all the lights on.


The next morning I had a text from the guy asking if he should continue to pine after me or if there was no chance of a second date. I nicely told him that I just wasn’t interested, but thanked him for the date and the gifts. He then sent me a message formulated like a public service announcement that said something similar to, “As of this DATE, Austin **** will no longer text Jessie. If he does, please contact customer service at 1-800-XXXX to fix the issue.” And thankfully I never heard from him again.

As for the gifts? Well, I brought all the snacks to work and left them in the kitchen with a note telling people to stop by my office if they wanted to hear a funny story about an awkward date. Luckily they weren’t laced with anything (hence why I tried them out on my coworkers – KIDDING), but that story has been forever remembered as the Creeper Snacks guy, since everyone stopped by throughout the day to hear the story.

And that, friends, is why online dating is terrifying. I have more stories, if you’re interested.

Linking up with Meg.

Let me know if you’d like to hear about my other crazy online dating story! It’s not as long as this one, but it’s still pretty creepy. Do you have any funny dating stories? 


    • Jessie says:

      Oh, don’t you worry. Laugh away! 🙂 I figured the best thing I got out of that date was the story. Though the tape was helpful in the move. 😉

  1. Sam says:

    At least you got a great story out of it! I’ve had a few very… interesting encounters with online dates, as well! Your’s takes the cake… er, fruit snacks, though!

  2. Pingback: Just Jessie

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