The other day, I was scrolling through my Facebook feed when something a friend posted stopped me in my tracks: a link, without comment, to a GoFundMe page titled “Help Me Find My ‘Person’ Organized by Jennie Dwin.” The accompanying photo was of a nice-looking, smiling woman with the word “SINGLE” stamped on in big, purple letters.

I’ll be honest, my first reaction was what. the. fuck. Clicking on the link confirmed my hunch for what this was: a crowdfunding attempt to help a single lady land a husband. As the GoFundMe page explains, Jennie Dwin is a 35-year-old Jewish girl who grew up in the suburbs of Boston and is currently living in Chicago. She’s got a great job at a digital marketing agency, great friends, two cats, and is “VERY single.” Frustrated with her lack of luck in the love department, Jennie set out to find a mate in a new way—through the services of a professional matchmaker. Only problem is, matchmaking don’t come cheap, and that’s where Jennie’s crowdfunding comes in, to the tune of $2500.

After my initial shock at the concept of asking friends, families, and strangers to pay for your chance at love wore off, I realized this wasn’t such a bad idea—in fact, it’s pretty endearing. After all, dating is actually the worst, as I’ve found myself throughout my years of Tindering (and Bumbling and JSwiping and OKCupiding and on and on and on). There’s nothing wrong with admitting that what you really want is a partner, and I appreciate Jennie’s chutzpah in putting it all out there for the whole internet to see.

I needed to know more, which is why I reached out to Jennie to ask some questions and get to the bottom of her epic “person” search.

Tell me about your dating life before starting this crowdfunding effort. How did you meet people? Were you on the apps?

I’ve tried paid and free apps (JDate, JSwipe, Tinder, Bumble, Match, EHarmony, etc.) and while they’ve worked for tons of people, they haven’t been successful for me. I’ve tried to get my friends to set me up but they don’t seem to know any single men (I find that shocking and hilarious). I’ve focused a large part of my life on work, especially when dating wasn’t going so hot which I know is essentially an avoidance tactic, but I’m successful in my career so at least I can check off that box!

What was the worst dating experience you’ve had? Feel free to name a few if you just really can’t choose.

It hasn’t been that bad, just hasn’t turned into anything! I have a good sense of humor so most of the experiences, while crazy, I look back on and laugh. I once went out with a guy who worked for NASA that I met on JDate. He didn’t attempt to make any conversation over dinner and when the check came and I reached for my wallet, he said “thanks” and got up and left. The waiter saw and said he felt badly for me. LOL—at least that guy cared!

Earlier this year I met someone on an app and we talked about how I loved New York style pizza (I lived there before moving to Chicago). We found a place in Chicago that had it and I was pretty excited. I waited at the bar for this guy and he never showed. The maitre d noticed and told me I shouldn’t put up with guys who acted like that and offered me a free slice of pizza. I felt too pathetic to take it. Can’t believe I walked away from free pizza!!

There was the time when I met a guy for coffee from JDate and he asked me if I go to the doctor regularly and get my vitals checked because it’s important that I’m healthy if I decide to get pregnant in the future (I mean, seriously!?).

jennie dwin crowdfunding
Jennie with her gay best friend at a wedding.

When did you realize you wanted to go the matchmaker route? How did you find this particular matchmaker?

I moved to Chicago for career advancement and for better dating options (dating in NYC was HARD). I’m working on the career piece but didn’t feel like I was making moves in the love department. I watch a lot of the show Millionaire Matchmaker which made me think that perhaps working with someone whose job it is to find me love might be a more efficient way to get to my target. Ultimately, I searched online and have found a matchmaking business in Chicago.

How important is it to you that you date/marry someone Jewish?

This is a tough one. My parents are religious and have always told me how important it is for me to date/marry only someone who is Jewish. I am not religious and would never date/marry someone who was—regardless of their religion. I want to marry someone who is a good person with good values. To me, religion is not necessarily a part of that. However, it would be way easier if the guy was [Jewish]. My parents are important to me—I would never want to disappoint them.

What have the reactions you’ve gotten so far to your GoFundMe campaign from friends and family ?

Everyone thinks it’s hilarious and isn’t super surprised. I’m shocked how many people find it empowering to speak up for what I want and admit that being in a relationship is important to me. I honestly felt more so that if my friends want me to get married, then they’re going to need to help me!

How did your parents meet?

Israeli dancing at a Hillel in Boston where they both went to college. They’ve said that they both knew they wanted to marry someone Jewish and went to a place where they can make that happen.

If this doesn’t work, what’s next?

Great question. I’m telling myself it will work because if I go into it thinking it won’t, I’ll likely pysch myself out of committing to it.

jennie and dogs
Jennie with a friend’s dog.

If you had to choose between the perfect man and your cats, which would you choose?

I adopted my cats when they were young and believe when you have a pet you commit to them for life. I would never do anything to harm my cats—and that would include rehoming them. If I had kids and met someone who didn’t like them, I would never give them away! This is the same thing. It would be irresponsible to do anything otherwise. The perfect man will love me for me and my cats—we’re a package deal.

What if the perfect man has cats himself? How many cats is too many cats?

I am a huge animal lover and if I could help every stray I would. I stop almost everyone on the street who has a dog—that’s just me. If I met a man who had his own cats and is able to take care of them well, then combining them with mine shouldn’t be a problem. I think the “technical” definition of a cat lady is someone single with three or more. At this point, my job is to make sure my cats have a healthy and happy life and I’m committed to doing that.

Read More