My Dating Diary :: The One With Brown Teeth, is Homeless and Loves Gouda

Oooooohhhhhh where do I start with this one!  This is hands down my worst first date, but also the most comical.  At this moment in my life I had been divorced for almost a year. I had very little dating experience because I was focused on other things.  I was finally ready to get back out there!  And what better way than to sign up for a dating app.  Pause for a deep breath lol

I met a guy who I started chatting with.  He had a great smile, blue eyes and brown hair.  He had recently moved to the area for his job, he was the VP of marketing.  We text for about 2 weeks before we met for our first date.  Everything about him seemed great and I was excited to meet him.

I walked into the restaurant for our date, he was already at the table.  He stood up to say hello and gave me flowers.  Flowers seems like a nice gesture right?!  I though it was… for about 10 seconds.  Then I realized, what the hell am I supposed to do with these flowers in a crowded restaurant?  There wasn’t room for them on the table.  I tried putting them on the bench next to me, but they were touching the person at the table to the right.  It seems like a nice thing, but no!

Next, he smiled at me and had brown teeth.  That’s when I realized all of his photos are him smiling with his lips closed.  Didn’t think it was something I had to put much thought into, but now I realize… a close lipped smile could mean brown teeth!

I should have left right then, but didn’t want to be rude. 

I began asking about his life, like where he grew up, etc. You know, the typical first date stuff.  I quickly realized that this man has lived a life of many complications and turmoils, non of which any of it was his fault.  He blamed his mom, his dad, his stepmom, his teachers, his ex girlfriend, his ex boss, etc.  He had many wild stories of things that had happened to him.  But where he is today and who he is as a person had nothing to do with any of his decisions.  Interesting!!  Victim mentality much!

I then asked him about his relocation and his job.  Turns out his “VP of marketing” was him working at a small local gym helping them put together flyers and small social events to bring in new customers.  As in: we are serving lemonade, bring in a friend and hopefully they will sign up for a membership. Ground breaking lol!! So to say VP of marketing is a bit of a stretch!

Then I asked him where he lives and does he like the area?  Well…… he had a whole story of how he was living with this girl that was just a friend.  Then one night she tried to sleep with him and he refused so she kicked him out.  (another story where nothing is his fault) Now he is living at the gym.  SO…… HOMELESS!! He literally doesn’t have a home.  He is living at a gym and showering in the locker room!  With no plan on when he will find an actual residence.

At this point of the date I wasn’t even angry about all the mislead information, I was more intrigued about what he might say next. 

As the server took our dinner order, he leaned over to her and whispered his order like a secret. Literally putting his hand up over his mouth so I couldn’t see and whispered it.  Then after she left he turns to me and says he likes more simple food and ordered the cheese quesadilla off the kids menu.  We were at this amazing Mexican restaurant and that is what he ordered. All I could think is, what the actually hell is happening?!?!?!

At this point I was struggling to keep the conversation going.  And that rarely happens, I can make good conversation with a wall!  I just didn’t want to talk to him any more and didn’t care if things got awkwardly quiet.  I mean… how much more awkward can things get.

In the small moment of quiet, he started a conversation about his love for gouda cheese.  It was literally the moment from ‘Forest Gump’ where Bubba is talking about all the ways to cook and eat shrimp ;). He went on and on for at least 10 minutes about gouda cheese…. I like gouda on my hamburgers, gouda in my mash potatoes, slightly melt gouda and drizzle it on my asparagus, gouda and salami with a cracker, gouda in my mac and cheese, gouda on a sandwich, gouda with my eggs, gouda fully melted tasted different than gouda slightly melted…..  I had no idea a person could have such a love for gouda and talk about it for so long.  It was so weird that the tables next to me were giving weird looks.  I gave the look back like – I know!!!

As dinner was ending, he asked me to walk to a bar next door.  He said he wanted to get me drunk so I find him more attractive.  Classy!  I told him I had an early morning meeting and had to go home.  I got into my car and got the hell out of there!!  

That is when I learned to meet for just a drink, not dinner, on a first date.  Always have an escape plan to leave quickly!  You never know when you will find yourself on a date with a homeless man ;)


Joggers: Abercrombie | Bodysuit: Abercrombie | Shoes: Similar Here & Here | Bag: Chanel, Similar Here & Here | Necklaces: Longer Necklace, Middle Necklace, Shortest Necklace | Hoops: Lana Jewelry, similar for $35

These joggers have become an instant favorite! I love looooove joggers! They are a staple in my wardrobe just like jeans. I have already worn these twice in the last week. The other time I dressed them down with this bodysuit and these sneakers. The fabric is amazing! They are comfy enough to wear all day, and also nice enough to be dressed up as well.

5 thoughts on “My Dating Diary :: The One With Brown Teeth, is Homeless and Loves Gouda

  1. Ohhhh man !!!! That’s such a crazy first date. lol I’m so happy you’re writing in your blog again. I definitely missed your post ♥️

  2. I loved reading this! I’m so sorry you had that experience though, that is miserable 😭 I thought you were going to say he photoshopped his teeth white or something 😂 that would have been so much worse!

  3. This is the best thing I’ve ever read!!!! 😭😭😭 I’m ready for more Rachel dating chronicles. But aside from that I’m so glad you’re out dating again let’s just hope there aren’t any more homeless men. You look stunning!

  4. Rachel, omg girl…. that is ROUGH! Lol… I’m also currently in the (online) dating scene and, I’ve gotta tell ya… there are a number of things you can gather from pictures alone before you even speak to someone. If they EVER hide any part of their face consistently through photos, something’s up… dead giveaway lol. I commend you for sticking that dinner out – I’m not sure I could have made it past the teeth. If that makes me a horrendous person, well… I guess I’ll wear that badge lol.

    Thank you for sharing this part of your life and journey with us. This dating road, while not the most difficult thing we can face in a lifetime, can be a hard one to travel. It’s helpful to know others are traveling it with you and that you CAN have a laugh about it, if you allow yourself to.

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