I Hired a Matchmaker
Over the last two years I've spent over $6000 for matchmakers to set me up on dates with the goal of meeting the woman I'll marry.
This series tells the whole story. Why I did it, how it works, and how it's going.
Part 1: Ready. Set. Date.
January 2020
By the time I hit 30, I was tired of hookups and flings. Sure, they were nice, but in the way fast food was nice: short term great, long term empty.
I was ready for a deep forever-relationship.
How did I know?
There's the external reason, and the internal reason.
Externally, I have a full life.
I have my shit together, as in, I’m not broke. I’m not struggling to pay rent while living on a floor mattress anymore. I wasn't going to ask Her to help me through my "figuring things out" phase while I floundered around broke.
Instead I run a business that makes me enough money to add extra guacamole to anything I want.
I've planted roots in my forever-city - Austin. I didn't want to wander into my 30's without a clear idea of where my long term home would be. As of this writing I'm 6 happy years into Austin with no plans on leaving.
I have strong relationships with lot's of people. I wasn't going to burden my partner with being my only emotional support human.
This is all to say that I wanted a great life before I met Her. I want Her to be
addition to a great life, not the final piece of an incomplete one. I want an abundant relationship where both partners want to be together. Not a co-dependent scarcity driven relationship where each partner needs each other.
Internally....I felt ready.
For most of my 20's hookups and relationships were ego validation. As a dorky video gaming high-schooler who couldn't talk to girls, hooking up was the ultimate ego boost. They were proof that I was worthy of love and desire.
I didn't need that anymore. My relationships with friends and family kept me emotionally secure. I had plenty of validation that I was a good person worth loving. I was tired of half-assed relationships with semi-compatible partners. I couldn't use people to fill my emotional scarcities.
These days a whole-assed, emotionally-rich partnership with a fully-compatible forever-partner feels way more exciting than a temporary fling.
Well that's cute, Alexander. Good for you.
But that's the easy part. That's all about me.
What about her?
The woman I'm looking for is beautiful, strong, funny, successful, kind, intelligent and confident. She loves good food, traveling, and has great relationships with friends and family. She's emotionally advanced and has a indescribable attractive energy about her.
Which brings me to the most difficult question.
Why the fuck would she choose me?
She'll have plenty of great suitors to choose from!
I needed to believe
I was worth choosing.
So here's my sales pitch to YOU, if you’re out there reading this....
Dear, Mrs. Concepcion (or whatever last name you choose, I'll be cool with whatever m'love.)
Here's why I'm the guy you want.
I'm emotionally mature.
I've scuba-dove into the sunken pirate ship of my soul and slayed many spooky trauma ghosts from my past. I promise to help you do the same.
My family is awesome.
I have a ridiculous and loving Cuban-American family back in Miami. You won't like their politics, but I promise you'll love them as much as they'll love you. They will take you in the moment they meet you. Mom's been bugging me about you for a while. Dad will pepper you with questions because he's an overly intelligent lawyer and can't help it. My sister will take you out for fancy wines and help you pay less taxes.
My friends are great too. They’re entrepreneurs, nerds, foodies, cooks, yoga instructors, engineers, artists, programmers, gamers, professionals, and comedians.
I know how to be a good partner to women - platonic and otherwise.
Even though deep inside I'm still the chubby, awkward, video-gaming dork who couldn't talk to women, I’ve learned.
My sister made sure I learned to dress well, act like a gentleman, pick good perfumes, and how to bring my best self to the dinner table.
So no, you won’t see cargo shorts in my closet, and flip flops will be relegated to beaches and watery hikes.
I have great lady-friends who've shown me the horrors of dealing with creepy abusive dudes trying to get all up in their shit. That will never be me. I'll walk you to your car at night and growl at threatening looking street denizens.
As for all the other non-platonic romantic stuff? That's between us.
I'm kind. I'll surprise you with gifts. I’ll massage you when you’re sore and pick up food when you’re hungry.
Speaking of food….you'll eat well around me. Everyone eats well around me.
We'll lunch at grungy taco joints and dine at 3 Michelin starred restaurants you saw on Chef's Table.
I'll delight you with my cooking skills.
My smoothies will satisfy you. My hummus will humble you. My muhamara will mystify you. My scrambled eggs will elevate you. My butter coffee will bewilder you. My kombucha will cultivate your gut-biome. My cocktails will captivate you.
And that’s just the start.
I'm an adventurer.
I'll show you the world. We'll write haikus in Japan. We'll rave in Berlin till our feet fall off and muse about 18th century Neo-classical artworks in Paris. We'll re-capture Constantinople and stare at the stars in Joshua Tree. We'll ride camels in Morocco and plot to kidnap alpacas in Peru.
I'm brilliant!
I've read lot's of big fancy books and listened to thousands of hours of podcasts with the world's smartest people. My brain is packed with profound thinks. You’ll grow to love my brainy long winded semi-serious fully-ridiculous rants.
My words are as graceful as my thoughts are deep.
World History? Bring it on Caesar. Business? Let's talk about risk baby. Psychology? I'll tell you how it makes me feeeeeeeel.
I'm playful.
We'll fight monsters in dungeons and dragons, summon fire gods in Final Fantasy, and play disc golf.....Ok, probably not...I'll do those things. You'll grow to find these things features, not bugs.
We'll do acro-yoga, pop bottles on boats, boogie at music festivals, laugh at politically incorrect comedy shows, hike mountains, zipline jungles, and go to fungally assisted alternate dimensions.
I'm an entrepreneur
I built a six-figure business from scratch which is pretty cool.
But even cooler than the money, I control my time.
I built my life and my business so I can spend more time with the people I love - aka You. I can book one way last minute flights to exotic lands for months.
You'll rarely, if ever, see me stressed out. You won't lose me to my career. I won't work myself to death. Our kids won't grow up with an absentee father.
Last but not least, I'm hot!
You just so happen to be into tall ethnically vague brown dudes who look like they could turn water into wine, start a yoga cult, or ride amongst the Dothraki horse tribes.
You'll like that I take care of myself.
I lift heavy things up and put them back down so I can get stronger just in case I need to rescue you from a burning house. None of this dad-bod-bullshit for me. I promise to be as hot as I can for as long as nature allows.
In conclusion, I believe you will find my candidacy to be your forever-partner valid.
Hope to meet you soon,
Alexander
Part 2: Zero to Matchmaker
November 2020
Ok great. I'm a great dude with a great life ready to find a match.
Dating should be easy right?
Well....in theory. In practice...not so much. Here’s what I’ve tried so far.
Dating Apps
I know a lot of great couples who met on apps like Tinder or Bumble. If it worked for them, it could work for me right?
Not exactly.
I've been on Bumble, Hinge, OkCupid and Tinder for years. I’ve spent countless hours compulsively reading profiles, swiping, messaging and setting up dates.
It kinda-sorta worked early on. It didn't matter that I was broke living on a floor mattress. I would go on multiple dates a week, sometimes on the same day. I had a few brief flings and one relationship that went on and off for a few years.
And then somewhere along the way apps stopped working - not because I stopped trying.
I spent more time on dating apps. I paid for “spotlights” that gave me extra attention and dozens of "super likes" to make sure matches saw me. I swiped through thousands of profiles and sent countless messages without anything to show for it. Matches were rare. Matches that responded were more so. The rare match that would respond would stop after asking them out.
Years ago I could expect a few dates a month. That shrunk to one or two dates per year. The ironic part was that I had my shit together. I wasn’t living on a floor mattress scrambling to pay rent anymore. I started a business and managed to upgrade to a real bed in a nice apartment in a good part of town.
I would get frustrated, delete my profiles, uninstall the apps....only to re-install them months later to repeat the cycle.
But nothing changed.
I was failing for so long on dating apps I started to wonder what was going on. Do these thousands of women not want anything to do with me? Could I be that bad of a person?
Or was it the apps? Did going public mutate these apps into psychologically-manipulative algorithmically-optimized money-draining love-casinos that profited from people's desperate optimism? (hint: yes)
In the Wild
Most of my dating “success” has come from meeting women "out in the wild" via socializing, hobbies, going out, and through friends of friends.
Aka, the old fashioned way.
I know plenty of great couples who’ve met each other this way. That hasn't been the case for me. Most of the women I've dated I've met this way. But in the 12 years I've been adulting and hanging out with women I've only (briefly) dated one girl who I could have imagined marrying.
Not good frequency.
I don't rule out that it can't happen. I'm sure there's some cosmically random assortment of circumstances that would put us together at the right place at the right time.
But I'm not going to let that be my only strategy. If I was going to be serious about finding Her, I needed more than blind optimism.
I needed a professional.
Enter Matchmaking
Sophia was the first person I knew with a matchmaker.
She's one of the best people I know. She's a successful entrepreneur in her mid 30's. She’s kind, mature, cultured, emotionally intelligent, attractive, and fun to be around. Despite all that, she spent years dating without any luck. A partner here, a fling there, but nobody to start a family with.
Then she hired Jackie. Jackie worked for Tawkify, a professional matchmaking company. Plus, she was a mutual friend who ran in our same circles.
Sophia wasn't fucking around. She was tired of false starts. She was ready for the real deal. She dropped over $6000 on a 12 date package.
Her first date surprised her.
He was an attractive and successful entrepreneur in his late 30's. He'd done years of emotional work, embraced spirituality, and wanted the same things Sophia wanted.
It was a perfect match.
They were married within a few months and had their first kid less than two years after meeting.
That was fast!
And this wasn't some time-is-running-out-scarcity marriage. They're a great couple. It's obvious when I see them together. They love spending time together. Their personalities play off each other well. Their mutual affection is deep.
They were the right people who met at the right time, but it wasn't an accident. It was deliberate.
I was sold.
Of course, I didn't expect anything like that to happen to me so fast. I don't need to be married + kid that quickly.
But if it could work for her, it could work for me.
Sales Pitch to Myself
Sophia's experience turned matchmaking into a big blip on my radar, but I still had to convince myself. I knew it wasn't going to be cheap.
Was I really going to pay thousands of dollars to somebody for doing something I could do for free on Tinder?
Well, as I mentioned before, my other strategies weren't working. Meeting people in the wild and app-swiping was technically free, but cost a lot of time with little to no results. Besides, I have a business to run, a book to write, weights to lift, and friends to hang out with.
Time is expensive.
Then I asked myself; what else have I spent thousands of dollars on?
Car repairs, website designers, overpriced cocktails, accountants, gym memberships, music festivals, eating out, rent, and trips to exotic lands. If I pay for those, why wouldn’t I pay to meet the love of my life? I could afford it. I couldn’t think of a good reason not to.
In the end, my sales pitch to myself was simple:
Professionals hire Professionals.
Matchmakers are professionals. I'm a professional.
I'm hiring a matchmaker.
Beginning Matchmaking
I wanted to work with Jackie based on what she did for Sophia, but she had too many clients on her plate. Instead I got paired with another matchmaker in her company, Sarah (not her real name)
I filled out a form where I described everything about myself and what I wanted in a partner. Looks, life goals, hobbies, politics, age, ethnicities, etc. It was like filling out a more detailed dating profile.
We had our first zoom-interview to get things started. It was nice. Sarah was like a genie in a bottle that I got to describe my dreams and wishes to.
She detailed how the service worked. I could do the free option where she'd place me in a pool of matches where other matchmakers would draw from.
Or I could go the full matchmaker route where Sarah would go and act like a professional recruiter....but for love. She would search the internal dating pool, other clients, and their external networks. She'd then interview potential matches and set up with one she felt was a good pick.
She said I should expect one date per month.
Seemed reasonable. Like a genie in a bottle, I signed up for three wishes...I mean dates...for $2200
I knew it wouldn’t be cheap.
Matchmaking FAQ
I’ve told a lot of people about my match-making adventures. Here are some frequently asked questions.
How do matchmakers find matches?
They find matches the same way an executive recruiter would. They scan internal databases along with personal and external networks. They'll reach out to interview candidates to determine viability.
So some matches are paying clients and some aren’t?
Yes.
Some people I've explained this to think it's unfair if one person pays and the other doesn't.
It's a reasonable sentiment if you take absolutely zero time thinking about it.
Why would I want to limit my matchmaker's dating pool to a small number of paying clients when she access to a much broader pool?
What if you meet The One early on in the middle of a package? Do you get a refund for unused dates?
Depends on your agreement.
I recommend making sure whatever matchmaking service you sign up for has a reasonable refund clause for unused dates.
Can you see a picture of your date before meeting?
These are typically blind dates, so no. Identities are kept secret.
Who sets up the date?
The matchmaker.
Does the matchmaker pay for the date?
No. If they did you could bet you ass I'm buying the most expensive bottles of wine on the menu.
So that means that I'm paying for the match and dinner? Isn't that expensive?
Yes. Expensive problems have expensive solutions.
How does feedback work?
After a date you fill out a firm asking basic questions about how the date went, what you liked and disliked, and if you'd like to see the other person again.
If both partners say yes, then numbers are exchanged and you can take over from there.
Can you match with people in other cities?
If you want. If I lived in a podunk town in the middle of nowhere, I’d ask to be paired with people in different cities. I live in Austin, a city teeming with beautiful attractive women who have their shit together. I don’t need to look elsewhere.
Part 3: The First Dates
November 2020 - April 2021
Now that I had a matchmaker. It was time to start dating.
Date One - KC
I knew the odds of meeting my forever-partner on the first like Sophia were low, but I was excited to get started.
Sarah booked a table at a nice neighborhood restaurant on South Congress. I was freshly trimmed, nicely dressed and scented with fancy cologne.
I sat down and ordered myself a drink. When KC arrived my excitement deflated. Immediately I recognized the problem with blind-dating.
I wasn't attracted to KC at all.
My matchmaker had an idea what my type-was. She had pictures and descriptions to go off of. But had to guess if I'd be attracted to them.
It wasn't KC's fault. She was a great person. She was kind, intelligent, creative, and emotionally connected; all things I asked for. She was great on paper, but not somebody I would have matched with on a dating app.
We got a light snack, a drink and discussed typical first-date things. It was a nice, but short date. It was clear there was no chemistry and we left knowing we wouldn't go out again.
Date Two - LP
LP was more attractive than KC. She was bright, bubbly, and excited to be there. It was her first time on a blind date. The date was at one of my favorite restaurants: Launderette. We ate well and bantered. She was a better external match than KC, but not internally. There wasn't much to talk about below typical first date surface topic. I was into entrepreneurship, history and festivals. She was into Disney and reality TV.
But still, we both agreed to a second date.
We met next for a light hike through a park.
It was pleasant, but it confirmed what I initially felt: there was no chemistry. She sensed it too. We decided there wouldn't be a third date.
I was 0 for 2 with one date left.
I wasn't happy with The Service so far. I was paying way too much money to go on dates with women I wasn't even close to compatible with.
Date Three - FF
One day Jackie texts me:
Hey! I've got a friend I think you should meet.
Jackie wasn't my matchmaker, but paired me anyways with one of her friends for free.
Bonus freebie date! Cool!
FF and I met at a hookah lounge in South Austin. She was cute and very fit. Nice. I learned she was a fire-fighter. My reaction was immediate.
Oh! You're a water Pokemon!
I thought it was hilarious.
FF....not so much.
.....
How old are you? she responded.
Alexander: Uh….....31.
She was 37. I had a feeling we were already check-mated.
Despite this the date went well. She had great energy, loved adventuring, and had a super interesting life. We were into each other, at least in a kinda-sorta way.
We agreed to go out again.
But after some failed back and forth planning the energy was gone.
We were in two different life phases. I was looking for a fuck-yeah relationship. This was not that. I wasn't going to waste her time with a relationship we both knew wasn't going anywhere.
We didn't meet again.
Date Four - JV
Date Four was my last match for this package. It would determine if the $2200 I spent would become a relationship or a sunk cost.
We met at my favorite restaurant in Austin, Suerte. The second I saw JV I knew this date wouldn't be like the others.
Who the fuck is this?!
I thought. Really? I'm going out with her?! Fuck yeah!
JV was stunning. She walked elegantly dressed with a quiet confident grace. She had amazing energy. She was engaging and seemed just as happy to be there as I was.
No fucking way. I couldn't believe I was going out with her.
She was why I hired a matchmaker.
JV was an experienced traveler like me. She had a successful (and lucrative) career doing what she loved. She was the first person I've met as obsessed with food and restaurants as I was.
We jumped deep past the typical first date conversations and bore into each others souls. I shared things with her I never shared with some of my closest friends. The more I revealed the more she wanted to know.
I was imagining the adventures we'd go on, the meals we'd share and the deep conversations we'd have. I was imagining a future together.
It was like the most I've ever connected with someone on a first date.
She blew me away. I've never gone a date like that before.
Holy shit. I'm going to start dating one of hottest women I've ever met. This is awesome!
I went home and rushed my feedback to Sarah.
10/10! Home run!
Now it was time to wait for JV's feedback. I felt she was as excited to see me as I was to see her. I also knew she was traveling that weekend so it might be a few days before I heard back.
Next day....nothing. As expected.
The day after that....nothing. She's on vacation.
The day after that....nothing. End of the vacation!
The day after that....nothing. I felt a cold sweat.
And then I heard back.
Sarah: Sorry, there won't be a second date. She did not feel any romantic connection.
I was stunned. I played the date back in my head over and over and wondered what went wrong. If you asked me hundred times how the date went I would have said amazing every time. I could have sworn she liked me.
....she didn't feel ANY romantic connection?
That thought played on loop.
I felt exposed....almost violated. It let someone into my soul and got rejected.
How could I be so off?
This was another problem with matchmaking.
I was being set up on dates with amazing women.....who could then go on to reject me. Recognizing and communicating mutual incompatibility was easy.
Being flat out rejected by someone I could have imagined myself marrying was not.
This was the first time that reality sunk - matchmaking was going to be harder than I thought.
Part 4: Dates 5-7
April 2021 - August 2021
My package with Tawkify ran out. I could stop, renew, or find another strategy.
I wasn't unhappy after the third date. I at least got one shot with a great woman. But I wasn't satisfied either. Sarah, my matchmaker, was nice and professional, but we didn't have much rapport. We only spent about an hour and a half talking on zoom.
For the kind service that was attempting to pair me with the love of my life, I wanted my matchmaker to know me. Like....really know me. I wanted her to understand everything from my lovable traits to my quirky faults. I wanted her to be confident that she could tell the difference between a decent match and an amazing one.
Plus, I didn’t like Tawkify’s business model. I sensed they were more interested in their quota than pairing me with a good match.
I wasn't going to spend thousands so I can be paired with mediocre matches.
Around this time Jackie went off on her own and started her own matchmaking business. I hired her directly.
When I told Sarah that I wouldn't be renewing she a short and corporate cordial goodbye.
Thanks and wish you the best of luck.
That's when I knew leaving was the right move.
Enter Jackie
Jackie had an advantage Tawkify couldn't match.
We're friends. We're about the same age. We run in the same circles. There's a reasonable chance that my future-wife could be in our mutual friend-orbit. We live in the same neighborhood. We can get tacos and bullshit while she gets to know me, get a feel for my energy and better understand who I'm looking for.
In short, I trust her.
I signed up for a 6 date package. I spent a little more-per-date than I did with The Service, but I was fine with that. Paying more meant I'd get more time with my matchmaker and a better resulting service.
We agreed to no monthly quotas. Finding a fuck-yeah partner wasn't something that happened with strict deadlines.
It was time to get back on the dating horse and try again.
Date 5 - MH
MH was the first girl Jackie matched me with. She was cute, tall, and dorky, but in the fun endearing way. We met at a cocktail bar in East Austin. The date was nice. The banter was fun and intellectual. We went from science fiction to history to world travel - all topics I love talking about.
I left feeling we had a good connection, but it wasn't the same intensity from what I felt in Date 4.
We rated each other a 4 out of 5 and agreed to a second date.
We were an hour away from that second date until she messaged..
MH: I'm feeling anxious about this date. I don't think it's a good idea for us to meet.
Date 4's rejection felt like being stabbed. This felt like an ant bite. It stung, but briefly. I wasn't bothered that she didn't want to go out again. It meant she was right. We weren't compatible. I was looking for a 5/5 relationship, not a 4/5. Going out again wouldn't have made sense.
Matchmaking Record: 0-5
Date 6 - RB
Date 6 wasn't fancy like the other dates. We went to Nickel City - my home-base bar in East Austin. They have cheap drinks, good cocktails, baller sliders, and excellent wings. If you don't like Nickel City, you don't like bars and you won't like me.
RB floored me moment I saw her. She was gorgeous. She had bright blue eyes, sandy blonde hair and wore cute overalls. She was hot, but in a down-to-earth-I-fuck-with-Nickel-City kind of way.
She had a rare radiantly kind and loving energy. It was the kind of energy that set off romantic alarm bells in my soul.
We quickly discovered mutual connections. She was good friends with some of the most important mentors in my life.
Oh, you know so and so! No way!
That kept happening over and over.
We read the same kind of books and listened to the same types of podcasts. Talking to her was like tunneling into the deepest trenches of my brainy and emotional rabbit holes....and finding her there waiting.
I had a big bright smile the entire date. At one point a breathed a heavy sigh of relief.
Finally.
I thought.
She could be the one.
I've never met anyone like her. She had a calm confidence about her life, where she was, and where she was going. Her goals, dreams, and ambitions were my goals, dreams, and ambitions. She saw life the same way I did.
After the date I ran home to send feedback.
Likes: Everything
Dislikes: Nothing
Rating: 5/5 10/10 1000/1000
That weekend my sister was visiting. She saw me right after the date.
Sister: Whoa! I've never seen you glow like this.
She was right.
This girl is marry-able, I told her.
It was time to wait for feedback.
I was anxious. RB made me forget JV from Date 4 ever existed. I was at an inflection point. Either I'd be building a relationship with a potential future wife, or I'd be crushed and sent back at square one.
Next day.....nothing.
The day after that.....nothing.
3rd day....4th day....nothing.
That familiar cold sweat returned.
5th day.....
Jackie: Hey Alexander. RB left you amazing feedback....but there will be no second date. She did not feel a romantic connection. I'm sorry.
...
...
...
My stomach dropped.
I was so close....but the closer I got to a bullseye the worse it felt when I missed.
No romantic connection.
I stopped working. I couldn't take phone calls. I laid on the couch for the rest of the day in shock.
How could I be so off?
I could have sworn we had a connection. What did she see...or not see in me?
The rejection reminded me when Monique in 5th grade laughed at me in front of our friends after I told her I liked her. I was a kid again whose heart was ripped out and crushed.
What's wrong with me? Am I not good enough?
I know I can have great platonic friendships with women. The evidence is there. But I was starting to doubt that was possible for a romantic partner.
I imagined the kind of guy RB would have said yes to. What was he like? Was he kinder, wealthier, more successful or better looking than me?
Would I ever be good enough?
This is where having a good matchmaker is important. They're the coach pumping you up back up in the corner after you've been punched in the mouth.
Jackie: This is the tough part of the job. This will happen. Don't worry. This happens to almost everyone. You're not alone. It's not you. You're fine. You're good looking, smart, kind, mature, and you have your shit together. You're a catch. I'll have your next match soon."
Aye aye love-captain. I'll follow your lead.
This was what I signed up for.
I was setting myself up for repeated failure and rejection so that I can maybe, just maybe meet the girl I'll spend the rest of my life with.
Bumble...Again
After RB's rejection I made a new Bumble profile...again.
Maybe...maybe it would work this time. I added my best pictures and answered every question so the algorithms would grace me with their magic.
I bought upgrades, infinite swipes, and dozens of super likes.
I swiped, super liked and swiped some more everyday for a month.
I got 5 matches.
Of that 5, one messaged "Hey", and then unmatched the next day.
I deleted my profile...again. Forever? I don't know. I hope so.
Date 7 - SM
I've got someone for you!
Jackie texted me 6 weeks after the RB date.
She set us up at a new wine bar in East Austin.
SM walked in and my eyes bulged. She was a beautiful brunette with a lean dancers body and an elegant taste in clothes.
Hell yeah. I'm in.
With a Malbec in my hand and a rose in her's we sat in a giant gaudy blue couch and began the smoozing.
SM was a therapist. She liked chili cheese hot dogs. She gave squeaky ducks to people tripping too hard at techno festivals. She specialized in fore-arm putters in disc golf.
Fucking Jackie: I thought. She found me a hot empathic dancing disc-golfing techno-goddess.
Back-to back-bullseyes.
This is why I hired Jackie. She knew who I was looking for.
I was comfortable around SM. The date was a lively yet relaxed conversational tennis match of witty banter, deep intellectual insights and energetic connections. She smiled the entire time.
My kind of date. My kind of girl.
The next morning I gave Jackie my feedback. All positive. Second date please.....I hope....
The day passed and SM hasn't given her feedback yet.
I've been here twice already - great dates with amazing women who I was positive I'd see again. I'd send my feedback....and wait.
A day later I find out….she wants to go out again.
Sweet!
We exchanged numbers texted.
We text-bantered for the next few days while coordinating Date 2.
I was pumped. This was going to be the first second-date I was excited for.
Me: Does this work?
SM: That sounds awesome! But no, I have plans.
Me: Does that work?
SM: No, I work then.
Me: Ok, let me know when you have time next
No response
Me: Does Friday night after 7 work?
SM: Maybe, I have an event but I'll text you in the morning.
I kept waiting. Days passed...and nothing.
The cold sweat came back. I didn't know what to do.
Do I message more?
I've definitely been that-guy before: the increasingly desperate text-way-too-much-guy in the past.
I wasn't going to be that guy again.
But I also couldn't tell if SM was waiting for me to message about the next date.
Maybe I was fucking up by not-texting.
I was totally lost. It was killing me. A week went by and nothing.
Reality sunk in. She ghosted.
The other rejections were rough, but explicit. I at least had closure. I could deal with that. Being ghosted was a poisoning stab who pain lingered. Of all the rejections, this was the worst. There was no closure. I was angry and falling into despair.
What the fuck is wrong with me? Why does this keep happening? I'm the only common denominator. It must be me. It must be me. It must be me. There's something wrong with me.
The loop kept playing in my head.
I didn't realize people in their 30's still ghosted. I couldn't believe a therapist, somebody professionally attuned to emotional pain, would ghost like that!
It felt immature....even cruel.
This happens to everyone! I promise it's not you. Jackie tried to reassure me.
I wanted to believe her, but I couldn't. The contrary evidence felt overwhelming.
Nobody I wanted to see again wanted to see me again.
I spent the next week in a deep funk. I barely worked. I barely wrote. I lost hope.
The pain wouldn't go away. I couldn't wait any longer. I needed closure. I knew I couldn't wait for SM to give it to me. I needed to create it.
I needed to send one final message. I wanted her to feel terrible. I wanted her to feel what I felt.
But I wasn't going to incinerate the world so I could prove a point.
Here's what I sent.
Hey SM, I really enjoyed meeting you and hoped we could go out again but I've got the feeling the reverse isn't true. For the sake of my own closure, I wanted to send you one last message. Have a great week!
The moment I hit send my psychic fever broke. I purged the dark energy poisoning me.
SM never responded, but I didn't need her to.
I had closure. I could move on.
Being ghosted sucked, but I knew I was spared from dating someone who didn't have the maturity, courage, or basic decency to communicate.
The woman I was looking for would never do this.
I was at peace and ready for the next match.
By now I was 7 dates in. Out of those 7, I had one second date, and no third dates.
I deleted my remaining dating apps and wasn't having any luck meeting dates in the real world. My dating life had flatlined.
By any metric this was turning out to be a complete and total loss.
Dealing with rejection
The constant rejection was brutal. Ever rejection was getting worse. But I learned to process it. I wasn't going through this alone. I kept friends and family in the loop. I'd tell them about each date, how excited I was, how the dates went....and how there wouldn't be a second.
I never hide how awful the rejections felt. I couldn't let these feelings fester and rot me away from the inside. Sharing purged the dark energy.
And If I couldn't get out of my head, I would get into my body. I would lift and huff and puff until I cleared my head.
Will all this be worth it?
I have no idea.
I have three dates left to find out.
Part 5: Conclusion?
August 2021 - July 2022
I believe in aliens.
Odds are amongst the bajillions of planets along bajillions of years there must be life somewhere other than Earth. I also believe we'll never find out. The time and space between life-supporting planets is too big. The odds we'll meet aliens in our lifetime is effectively zero. Instead we're stuck alone on this planet wondering "what if".
This is a (statistically dramatized) expression of how I feel about dating at this point.
Jackie, maybe blending a sense of professional pride and/or feeling bad for me, was sending me on more dates than we agreed to. I could go through the details of each date like before, but that would be redundant. Instead I'll skip to their outcomes.
Date 8: No attraction (But we did become friends)
Date 9: Good date. No compatibility.
Date 10: Good date. No compatibility.
Date 11: Total mismatch.
Date 12: I liked her, but she declined date 2.
Date 13: Attraction, but no chemistry.
By every imaginable metric matchmaking was a total failure.
As of this writing its been two years since I started. Between date-fees and dinners I've spent around $7000 to go on 13 dates. I’ve gone on one second date (which didn’t need to happen).
I lost hope in the process. This felt like datemaking more than matchmaking.
For every date either I wasn’t interested in them and/or they weren't interested in me.
I have nothing bad to say about the matches (except for the ghost from before). They've all been smart well-rounded women who had their shit together.
I'm sure they'll be great partners….for other people.
Matchmaking wasn’t working. I wouldn't have gone on most of these dates had I seen their pictures or read their profiles. I suspect the matches would have felt the same way about me.
Maybe she was hoping we'd get over the low-attraction thing after getting to know each other after a few dates.
That wasn't going to happen.
I wasn't going to date somebody I wasn't attracted to nor would I date somebody who wasn’t attracted to me. I'd rather stay single and have platonic girlfriends.
I knew Jackie was trying her best. I knew she succeeded with other people. But I started believing I was a special case - that there was something special about me that made me unmatchable.
In that time I did the last thing I wanted to do - I went back to dating apps. For months I swiped, messaged and messaged some more. As usual, Bumble went nowhere.
In what felt like a miracle I met someone on Hinge. We went out...and kept going out more.
Cool!
But "we're totally going to date" became "we’re never going to see each other again" in two months.
Meeting people in person wasn't any better.
I lost count of messages approximating "I really like you...but".
Overall, life is fine. Business is fine. My friends are great. I do lot's of fun shit. My house is in order.
But fuck me, dating has been a total disaster. Worse has been the thoughts vortexing in my head.
Wait, HOW many women have turned me down?
I'm not good enough.
How many hundreds or thousands of women have ignored me on dating apps?
Not even a professional matchmaker could get me a match!
Should I just accept staying single?
Am I being unrealistic?
Maybe I don't have a match.
If I like her she won't like me back
Why bother trying?
Am I really that unattractive?
I'll never be more than a friend.
Something has to be wrong with me. Matchmaking isn't working. Dating apps aren't working. Meeting people in person isn't working. There HAS to be something wrong with me, right? I'm the common denominator!
I should give up entirely.
I gave up finding the person I’d marry. I just wanted to go out with somebody who wanted to go out with me. Even that felt like a stretch.
All of this feels humiliating in a high-investment-zero-return kind of way. It’s like that grade-school-never-got-picked-for-kickball embarrassment. It’s been a slow Chinese-water-torture erosion of hope.
I don't have the emotional sobriety to process this all yet. This is partly why my matchmaking budget has become my therapy budget.
The only reason you're reading this is the catharsis I get from writing. Somehow publicizing my dating failures beats allowing the energy from poisoning me from the inside.
In starting this series I had something resembling a heroes journey plotted out in my head. Some initial tension, a fateful decision, a string of difficulties punctuated by a happy ending. Maybe I would be an inspirational guinea pig for someone going through the same thing.
That’s not this story. At least not yet.
I do know I won't spend another dime on matchmaking.
I don't know where things go from here. Giving up feels merciful, but depressing.
Maybe I'll take my therapist's advice and take a break from dating.
Maybe I just have to hope for aliens.