I Concocted My Own Real-Life ‘Bachelorette’ Season to Find One Gem Among 40 Guys—Here’s What Happened

i concocted my own bachelorette season: woman holds phone, surrounded by online dating profiles, hearts, and roses
Dasha Burobina/PureWow

Nancy Rosefield has been a lifelong fan of The Bachelor. After moving to New York City to pursue a career in book publishing, she was ready to fall in love...and to host her own reality dating tv show. The self-described hopeless romantic recounts the five months, 40 men, 13 dates and one mega spreadsheet that led her to the one who did, indeed, accept her rose.

This interview has been edited for length and clarity; pseudonyms assigned for privacy.

I’m a hopeless romantic. To live in a world where you think, I’ll hop outside and fall in love today—that’s kind of a nice thought to have. These romantic expectations are usually ludicrous, and I have come to terms with the sad, sad fact that I won’t wake up to someone singing me a song outside on a boombox unfortunately—but part of being a hopeless romantic is holding on to the thread of possibility that just maybe, real life will defy all odds for the rom-com scenario of my dreams. Last fall, I was watching The Bachelorette and wasn’t really enjoying the season, so I decided to, well, become the bachelorette myself. I was going to set up multiple dates, dating game show style, to find my potential match. I figured that even if nothing came of it, at least my friends and I would have some good laughs. Besides, the dating scene in New York is rough. I mean, have you heard about the a Facebook group called “Are We Dating the Same Guy?” where nearly 90,000 girls can warn others about their toxic exes? If that’s the situation we’re looking at, might as well make it a good time.

A Complete List of Every Single Past Bachelor, Ranked

This Is So Much Harder Than I Thought

Before I could officially start my season, I needed to assemble “the cast.” One night, I gathered my roommates in our living room, connected my laptop to the TV and went through various online dating profiles on Bumble and Hinge to find the lucky contenders. We ended up with 40, including Canada Man and Dr. Doof (yes, they all had nicknames—how else was I going to keep them organized?), whom two of my roommates were rooting for. The latter had reeled me in with our shared appreciation for Phineas and Ferb, so when he suggested meeting up the following week, I was sold.

I’m a people person, so starting conversations is easy for me. Chatting up 40 people? I can do this. However, keeping the conversation going is where things got difficult. Not many were able to hold conversations I would deem intriguing or nice. One guy would only answer “yes” to everything. A lot of guys would respond hours or even days later. Many answers were dry and didn’t include any questions about me. And sure, a lot of people hate small talk or just want to meet in person, but I need the chat time. I wouldn’t go on a date with someone without knowing more about them first, so small talk helps me decide if I want to pursue something.

To keep track of the contestants (who were unaware that they had just stepped into a reality show), my best friend created a spreadsheet that I shared with the spectators, aka my roommates and friends. Nine columns detailed names, nicknames, age, profile photo, chat vibes, date notes and rankings.

The One-on-Ones

After a week and half, I narrowed down the dating pool to eight and in total, I went on 13 dates with these guys. I had the highest hopes for The Stache, a 23-year-old engineer. He earned my first impression rose. He’s funny, sarcastic, did acapella, has a great personality, I wrote in the spreadsheet. But sadly it was not to be. In person, The Stache was pretty judgmental about...everything.

Another one of the early contenders was a 24-year-old law student whom we nicknamed Dr. Doof, thanks to his pickup line. TOP 3! He’s funny and great and that pick up line? Like, when’s the wedding?!?!? I wrote. Our first date was at a board game café, and two of my roommates tagged along incognito—somewhat for protection purposes (you never know these days) but mostly because they just wanted to see The Bachelorette play out IRL. What can I say? My viewer ratings were high. The first date went well, but everything fizzled on date two. There just wasn’t that spark the hopeless romantic in me needed to keep going. So they were both out...and then came Canada Man.

He Isn’t Here for the Right Reasons

Right off the bat, I could tell he wasn’t too serious, but one of my roommates was rooting for him, so why not? I had to fulfill my bachelorette obligations. The chemistry was, once again, off the charts, I wrote after date two. We had a great, sarcastic banter going and he was funny and the man could cook! We decided to meet up for date three at a ‘70s-themed bar. The spreadsheet entry went as follows:

Made out on a waterbed, haha. Made out a lot. Wish there was more invigorating conversation, it’s too playful at times but the kissing is nice. Once again, made it very clear how much he wants to sleep with me so had to tell him that that would not be happening and he proceeded to say that “he’s not looking for something serious” despite LITERALLY swiping on me when I put I was looking for a relationship. Why did you bother me then Canada Man???

Making out on a waterbed is kind of funny. Saying, “I got to make out on a waterbed in my 20s” is a cool sentence. But then he invited me to his apartment for a hook up, and I’m the kind of gal who likes to take things slow, so I said no thank you. He asked if we could be friends. I said OK, but I knew it was the sort of “can we be friends” that just meant we’re parting ways on good terms, never to see each other again.

At this point, the holidays were rushing around the corner, and I was ready for a break. So far, no one was deserving of my final rose, and no one had climbed the rankings. The spreadsheet was looking depressingly redlined.

Will You Accept This Rose?

Before I flew home, I matched with one last guy called Bread Boy because we bonded over our love of free bread at restaurants. He was a 24-year-old actuarial associate. We met for lunch at a Japanese-Jewish fusion restaurant and then kept in touch over the break, as we both skipped town. Once both back in the city, we continued to see each other.

12/10: Very nice date. I could tell he was nervous, but it was very adorable. We talked, had banter, went on a short walk after and it was lovely :) 12/16: Great date, had first kiss above the pier :) 1/12: Still dating Bread Boy! He's lovely and I no longer want to date other people! 1/28: Yeah, I think he's a keeper :) He just does the cutest things!!!

The “cutest things” seemed straight from the hopeless romantic playbook. He let me pick out books at store, and then read them over the winter holiday. He brought me a birthday present even though we’d only seen each other twice. During this time, my phone broke, and I was waiting for it to be repaired. I thought it would be sweet in this hopeless romantic way if he was sending me texts so that when I turned my phone back on, I would see messages from him. He did.

On our penultimate date before Valentine’s Day, he came back to my place to see the apartment, since I’d already seen his. While sitting in my room watching Amazon Fire Stick slideshows, the last episode of Community long over, he asked me to be his girlfriend in the most endearing, boyish way. My heart was exploding.

I thought my hopeless romantic expectations could/would never be met, but I’ve seemingly found a person who has done exactly that. Guess all us hopeless romantics need is a little luck...and our own reality dating show. I accept this rose.

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Nancy Rosefield

Freelance PureWow Editor

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