THE TIME I PLAYED MATCHMAKER ON TINDER
- THE NON-BLOG
- Mar 12, 2018
- 6 min read

If I wasn't heading down the career path I am now (whatever that may be), I fully believe I would have been a sex/couples therapist. I am that asshole who gives unsolicited, unwarranted advice about love and all messy things that come with it.
Luckily for my friend *Kelly, when she agreed to live with me, not only was she getting a roommate but also a live-in counselor.
Kelly holds herself to high standards and unfortunately people confuse that with being a prude. It's important to her that any man who comes into her life share her traditional values. And I respect that.
HOWEVER, Kelly had not been on a date since 2013 and as a friend that drove me insane. Not because I'm a crazy bitch (maybe a little) who gets overly invested in other people's lives, but because relationships are all too common of a conversation between us. The woman has a Pinterest board dedicated to her future wedding with 600+ pins for Christ's sake.
Kelly and I came to the consensus that it was time for her to take some action. Not necessary to find the man that would turn her Pinterest wedding dreams into a reality, but just to get some experience under her belt so she'll be a little less of an emotional wreck when the real thing comes.
God, I am an asshole.
My genius idea was to create a Tinder on Kelly's behalf. The unconventional approach seemed to take the pressure off her and let me play matchmaker. A win-win I suppose?
Kelly graciously (and cautiously) took me up on the task.
I downloaded America's favorite hookup app with the intentions of finding my friend a proper gentleman. From past experience, this seemed like it was going to be a challenge.
After scouring her Facebook and Instagram, I compiled the photos to be used on her profile. A mix of adventurous but not wild, funny but not corny, family-oriented but not ready to pop out a kid anytime soon. You know? Just a nice girl.
Then came the bio. I tried to hit her biggest selling points and kept in mind what was important to her. Of course Kelly had the final say in her personal want ad.
It was officially time to begin pimping out my friend.

While swiping I was very considerate of what Kelly wanted in a potential date. Let's just say Kelly likes the saltine crackers of men.
After a few days the matches began rolling in. I was pleasantly surprised this unorthodox approach hadn't immediately scared men away. If anything they seemed receptive and intrigued with the method of a third party matchmaker. Of the dozens of men I messaged on Kelly's behalf, all of them (with the exception of a couple) were friendly and open to go through my obnoxiously extensive vetting process. Color me impressed with the male population for the first time.
What I did find strange (and mildly irritating) was the common thread that I was performing some type of charity work. Time after time, guys would message me saying "how nice" I was to be doing this for Kelly and "what a good friend" I must be. Like, hello??? This isn't the Make-a-Wish Foundation. I'm just trying to set my friend up on a date. If anything I am crazy.
I began to hone in on a couple potential prospects. One that especially caught my attention (and met Kelly's laundry list of standards) was *Adam. Catholic? Check. Non-smoker? Check? Educated and employed? Check. He seemed to fit the bill pretty well. I sent Kelly the pictures of him from his profile and she wasn't disgusted, so I'd say that was a success. After about a week of getting to know him through messaging and sharing all of Kelly's fantastic qualities, I decided it was time for Kelly to take things into her own hands. After a night of drinking I took Kelly's phone and added Adam's number to her contacts. There was no way she would have let me done so if she was sober, so I had to seize the wine-induced opportunity.
The next day Kelly mustered up the courage to send Adam a message.
"Hey Adam, it's Kelly! I hear from Olivia that we may be meeting at some point this weekend.??"
The exchange of messages between Kelly and Adam kept up for a few days. Soon followed a first date. A low-pressure dinner at a Broadway diner was planned for that Friday. As long as Kelly could make it through until then without a mental breakdown, my plan would be set into action.
Friday night came and nerves hit Kelly HARD. As she got ready I tried to ensure her everything would go smoothly, even though in the back of my mind I knew there was a slim chance I could have set my friend up with a serial killer. (Ehh... I'm sure it'll be fine.)
By five after 6:00 Kelly had walked out the door and I officially felt like a mother sending off my kin for the first time. [Cut to me sitting on my bed eating fruit snacks while watching conspiracy videos for the next three hours as I wait for Kelly to return.]
A few hours later I heard the doorknob jiggle and I sprung up like a dog who hadn't seen their owner all day. Kelly somehow managed to look happy and mortified all at once. At least I was certain I hadn't set my friend up with a murderer.
For the next hour Kelly gave the details of her evening with Adam.
Kelly made her way to the diner where she met a well-dressed Adam who just came from his cushy financial industry job. Unfortunately for the duo, a long line at the diner foiled their original plans. What was supposed to be a casual dinner quickly turned into a more upscale evening at a French bistro. Kelly's hand-me-down jacket, $2.99 JCPenney sweater, Goodwill denim skirt, and silver flats made her feel all too out of place. Besides the unanticipated fashion faux pas, Kelly seemed to have enjoyed her time out with Adam. The conversation was good, he offered to pay for the meal, and most importantly Kelly didn't barf all over the table from nervousness.
As Kelly got ready for bed, she casually mentioned something that seemed significant to the plot. While crossing the street she had a real life Cinderella moment as she briefly lost one of her flats. (Don't worry she went back and got it.) Was this a sign she had met her Prince Charming? I knew they were in the most infancy of their relationship, but how great of a wedding story would have that been if these two worked out?
The next day Kelly received a phone call from Adam to make plans for a second date. A second date at a pizza shop led to a third date at the MET. Although it all sounds lovely in writing, for Kelly there wasn't that proverbial "spark." She thought she'd go on one more date to be certain of her feelings toward Adam. A lackluster fourth and final date at an Italian market followed by dinner at an Indian restaurant confirmed Kelly's feelings. He was a dud.
Soon the text messages stopped and plans were no longer made. A mutual case of ghosting solidified the nonexistent future between this couple.
Once the dust settled, Kelly vowed to never go on another Tinder date. Although not a negative experience, there was definitely a bad taste left in her mouth from the stress of it all. She's a bit too traditional for Tinder anyway. I, however was proud of Kelly for putting herself out there and trying something new.
I don't know if there is a life lesson to be learned or moral from this story. For Kelly she'd probably say, "don't let your crazy roommate set you up on Tinder." For me, I think there's a lot to be said about trying something that makes you uncomfortable every once in a while. Worse comes to worst, you get some free meals out of it.
* indicates a name change to protect anonymity and prevent further embarrassment
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