Single and Ready to Mingle – This is What Happens When You Go on 9 Dates in 1 Week


When you’re sad and single, you are told to get on the apps at least twice a day. Additionally, the prior approximation is probably an understatement.

It had been almost eleven years since I’d played the field. I had been in a long-term relationship that recently ended – and the guy I dated prior to him, was a repeat from college. So, at this point picking up anyone new was not exactly my forte. It’s funny when you’re in a relationship you get so good at fending off the men – you feel like they’re creepy and always wanting to do shitty things like introduce themselves and buy you drinks. Then all the sudden you’re single and it’s like, where are all these assholes I’ve been running away from for ten years?

Luckily, there’s an app for that.

My new best friend Bumble stepped right in and said, “Jenny, don’t worry. I’ve got this” and swiftly set me up with nine dates over the next seven days.

“He’s literally parting the crowd as he’s walking toward me.”

I devised a very simple plan: I decided to go along with whatever they asked me to do in addition to wearing the exact same outfit on every single date. It would be a closed door experiment with the only variable being the guy. Don’t I sound fun?

It was a sunny mid-summer Monday around 6:45 pm and I was headed to my first date. He asked me to meet him at coup d’etat. I had never been there, and that wasn’t by accident. But, I figured, 1st date = practice date – go throw some moves at a stranger and see what sticks.

I park at the meter, jump out of my car and as I start running across Lake street someone who I am forcing to slow down because I didn’t want to use the crosswalk screams out, “Stephaniiieeeeee.” I, of course, didn’t turn around due to the fact that my name has been Jenny for the last 33 years. I walk in, don’t see him anywhere and sit down at the bar. I order a drink and wait.

He appears. I jump off my bar stool and say, “Date no. 1?” (Not really, but we’ll keep these cool cats anonymous). He’s totally cute and seems silly and genuinely happy – I’m excited.  He’s been making me laugh for about fifteen minutes now and he gazes into my eyes and says, “I was hoping that was you from earlier.” I scrunch my face and say, “Wha?” He says, “I saw you running across the street – I called your name but you didn’t hear me.”


So, I say, “I didn’t turn around because my name isn’t Stephanie.”

There was silence. He’s no longer gazing at me – he just looks terrified.

Then, I say, “It’s Jenny.”  

I wasn’t actually offended – he was my practice date after all as well as one of nine for the week – so, oh well. Practice date, check.

Date no. 2 was at 9 pm – same day. I jump in my car and head straight to Parlour. I was the first one there. Again.  

Then I see him – the sexiest man in the world. Gorgeous face, tailored white shirt, perfect teeth.  

He’s literally parting the crowd as he’s walking toward me.

He’s just fascinating. He has an accent, looks me in the eyes and he’s entrepreneurial. I mean, come on. It was a great date, the bar was set.

Date no. 3 was at Eat Street Social. I don’t notice him when he arrives but he walks up behind me and touches my shoulder. I turn around and he is the preppiest most adorable man with crystal clear blue eyes with thick, dark hair and a mischievous side-smile. It was one of those dates that you didn’t want to end and when our time was up, we walked outside, told each other how great we were and said goodbye. I patted myself on the back and decided that I was really good at dating.  

“I mean, he can’t be real, right?”

But, then he kissed me. This didn’t happen on my practice date and I was completely unprepared.  

So, I did what any pulled together 33-year-old would do when someone they are totally into kisses them – I said nothing and turned away, then literally ran to my car. Yeah, my car was like, three cars away from where we were standing and I just ran. I got into the drivers seat, put my hands over my eyes and silent screamed for about thirty seconds, then drove away. So, the first new kiss went really well. Again, FML.

Dates 4-7 were fine but overall I would label them as slightly awkward and boring. It was less “long looks” and more “let’s split the check and leave.” So nothing to write home about there. 

I was hoping that the last two dates would cancel. I was exhausted and my “opening up” quota had been reached for the month in just a matter of days. Dates no. 8 + 9 both took me back to Eat Street Social – the bartenders were extremely great sports and never once acknowledged that they had heard my life story three times in a row nor did they mention that I only owned one outfit.

No. 8 was Venezuelan and had his MBA from Harvard. He was leaving for a work trip to Europe in a few days and wouldn’t be back in town for three weeks because on his way home he had to stop in Manhattan to run the marathon. Did he secretly find my “perfect person” list that my type A friend, Bethany made me write of who I wanted to date next? I mean, he can’t be real, right?

No. 9 was a radiologist who lived on the streets of Paris for a while (an item I realized I forgot to put on the above-mentioned list after I met him). I thought it was odd how concerned he was with my sleep patterns. Every time we went out he asked me when I went to bed the night before and how many hours of sleep I had gotten. I went along with it for a bit but eventually, his “sleeping passion” was too weird for me. I wanted him to think I was a badass when I would respond with, “four.” Instead, I got a lecture about my brain and my skin. Every. Time. So, pass.

All in all, an exhausting week. I went on second dates with six of them and I actually got to know four of them, which I am going to claim as a success. Some became friends and one is still… around. I haven’t classified it yet – it’s been nearly a year so, to be fair, I suppose I should get to the bottom of that.

However, the worst date in history can’t be blamed on my girl, Bumble. This horrific evening came as a result of a “high-school friend hang-out.” We went to a bar that I don’t usually go to and while my friends were doing their thing, I stood at the bar. This nice guy who appeared to be a bit emo with a hat came up to me so we started chatting. I was more than willing to not be forced onto the dance floor so I allowed the conversation. He told me he was a scientist and it turns out we had the same taste in music. He seemed really interesting so I agreed to go out with him. He insisted on picking me up for our date and we were going to grab Thai food. I thought, what a fun choice for a first date. He picks me up in an original Ford Explorer without his hat. His hair was longer and stringier than mine and it went all the way down his back and it turns out he didn’t have any hair on the top of his head. The passenger door didn’t work so I had to climb through the driver’s side. We all go through ups and downs in life, so I kept a smile on my face. The back of his car was full of metal garbage, but the pieces weren’t in garbage bags. I didn’t look back there for too long, but if I remember correctly, there was an old amp and a massive battery amongst other things, all filthy.

“It was so awful. So bad that I have been frequently covering my face and squinting as I write this.”

We arrived at the restaurant and started going through the standard first date protocol. I eventually ask, “So tell me about your work, what kind of scientist are you?” He looks down casually and gets this weird look on his face and says, “Well, I’m not a full-on scientist. I just call myself a scientist.” I just stare at him. “I actually sort toxic waste, but I like to think of myself as a scientist while I’m doing it because it’s basically the same thing.” At this point, I literally could not hide a smile and I continue staring. Then he says, “I don’t want to do it forever, I actually want to move to Africa and start mining for diamonds.” I put down my fork, and sit back in the booth with no idea what to say next. I came up with, “That’s really interesting, sounds like fun. Okay, you know where I live, where do you live?” “Coon Rapids,” he replies. “Oh really, why did you choose Coon Rapids?” I ask. “Well, my parents live there.” “Oh, you’re really close to your family, that’s so sweet,” I say. “No, I actually don’t get along with them at all I just live in their basement,” he responds. This conversation took up the first twenty minutes of our date; the rest of the date was really similar and luckily, got to a point where I was very amused.

We leave the restaurant and I climb back into the driver’s seat. He somehow thought we were going to hang out a whole bunch in the future and insisted that he walk me to the front door even though I told him, “No, you really don’t have to” (THREE TIMES). But nevertheless, he gets out of his car, walks me to the door and attempts to kiss me. I was not in the – fine, I’ll kiss you mood and was literally bobbing and weaving away from his face on my front steps for about FIVE attempts. I mean, knees bent and ducking, it was awful. It was so awful. So bad that I have been frequently covering my face and squinting as I write this.

Bumble. It. Is.

That being said, following my week o’ fun, I swiftly stopped the apps. It turns out that it wasn’t that fun (for me) at that point in my life. I love dining and talking and bonding, but I had to have answers to all of these real questions… and people ended up wanting to have relationships with me. Which, I somehow never saw coming, for real. I got on the apps because I felt like that was what I was supposed to be doing, and it wasn’t until I was knee deep in dates that I realized I was in no place to be opening up to people with whole hearts.

Lately, I’m getting a lot more of the “Who are you dating?” “Well, aren’t you on the apps?” As conversation starters, so I am probably due to throw myself back out there again. I was recently told by a dear friend that my level of crazy was around 8-10%, which to me is basically normal if not boring… so, I think it might be a good time to give it another go. I’ll keep you posted.

Image sources: 1 / 2 / 3

BY Jenny Jorgensen - September 13, 2017

Leave a Reply

Loved reading this. Girl, you’re hardcore. Nine dates, even if they were just with family and friends, would drain me out!

Charmaine Ng | Architecture & Lifestyle Blog


I would like to see posts that are a little more real life about dating. The general story of Bumble for most women, I believe, is that it’s frustrating, time consuming, and hard on the heart. This sounds like some rendition of Sex and the City, which isn’t what I want to read.


We are all ears in hearing both the negative and positive stories in regards to dating, as I believe everyone’s dating experience is intrinsically unique. So if you or anyone else reading this has a different dating story to tell, please send it on over! I think it’s important to post a little bit of everything. My email is:


I am curious to what you mean “real life about dating.” Dating apps are the norm nowadays, especially when you’re no longer in school. My dating experience is very similar to Jennifer’s.


I haven’t dated for over 6 years and being recently divorced, I don’t know how to get back into it or if I even want to. But I loved reading this and enjoy hearing other women talk about their dating lives. Kudos to you for this experiment (lol) and please send some of those dream men to Indy.

Devin Law

This was THE BEST. I’m LOLing all over the place and trying to hide it at my desk. Such a great read!

This was such a hilarious read. To be honest I’m not great at dating because I end up just wanting to be friends with all of them (am I fussy? Probably). Which is fine if they want to be friends too, but I’ve definitely experienced the bobbing around to avoid a kiss a few too many times.

Nine dates?! Get it girl! I love your approach to this whole scene & those cocktails look pretty yummy too!

C’s Collection |

Such a great article! What about date #2!!! He sounds like a dream guy and you barely talked about him. Good for you, for getting back out there again. I often think if I had to get back on the dating scene, how nervous I would be to go on the Apps and find people. I feel like there are so many weird men out there – the sleep guy sounds a little OCD or something. Anyway, an eye opening experience nonetheless. Thanks again for sharing!


I wish I’d saved it because I’ve heard the same from others, but I once read an article about people mixing up the names Jennifer and Stephanie. I get jennifer all the time. Same number of syllables, same sounds, etc.

[…] 1. This is what going on nine dates in seven days looks like and Bumble, god bless […]


This was amazing. Having just recently entered the dating scene again as well after assuming that men were definitely just creepers who my friends had a strange attraction to, I totally know the feeling of, alright, let’s see where this goes. And then, after a single week, feeling pretty damn fine with being single again for a long while.


Amen, sister.

[…] Nine dates. Seven days. Whoa. […]

he show his He’s just fascinating. He has an accent, looks me in the eyes and he’s entrepreneurial. I mean, come on. It was a great date, the bar was set.


THANK YOU for this. I needed the laugh…and then realized I could have been the one writing this. My dating life to a T as of late. I literally subscribed 5 minutes ago and after only 2 posts in, i’m hooked.

Most-read posts:

Did you know W&D now has a resource library of  Printable Art, Templates, Freebies, and more?

take me there 

Arrow Alone

Get Our Best W&D Resources

for designing a life well-lived


Arrow Alone

the latest

Thank you for being here. For being open to enjoying life’s simple pleasures and looking inward to understand yourself, your neighbors, and your fellow humans! I’m looking forward to chatting with you.

Hi, I'm Kate. Welcome to my happy place.