Everyone has at least one epic dating fail if they have tried online or app dating in the last decade. Some of us have more than one, ‘ahem. My friends and family would tell you I have a unique gift of getting myself into some pretty hilarious types of situations. The story I’m about to share with you, hands down, makes my top 10 list of all time of such situations.

Earlier this year, I was power dating. I’d convinced myself dating was simply a numbers game and if I dated as many people as I could, I’d get to my number faster. Magical thinking at its finest. I was using a few different digital dating options, and this entertaining story comes to you directly from Bumble, a dating app where women basically have to make the first move after both parties have “swiped right”.

My theory with digital dating, after years of practice, is that once a connection is made, attempt to meet the person as soon as possible. I’ve found that talking and texting for too long prior to meeting is perhaps not the most efficient way to date. I say this because you can connect with someone via text or even on the phone, but totally bomb in person. My game plan is, once the connection has been made, to meet a date for a short interaction as soon as possible. This can be coffee, a drink, or a short walk. My only rule is that it needs to be in a very public place, and I don’t want to commit to more than an hour, because no one wants to be stuck on a bad date for multiple hours. Plus, if you do hit it off, it’s super easy to extend the date or schedule a 2nd one on the spot.

To protect the identity of the poor chap that is part of my epic fail, we’ll call him Stan Smith. (I happen to be wearing a pair of my favorite Adidas kicks as a write this.)

Stan and I met three days after we’d made a connection, exchanged a handful of texts, and one short phone call. (Hey guys, here’s a tip – some of us do still like to actually TALK on the phone and not just hide behind text messages or emails.) Charmed by his witty banter and after coordinating schedules, we’d agreed to meet at the new bar at the W Hotel in downtown Bellevue at 7pm on a Saturday night. I styled my hair just right, selected an appropriate first date meet-up outfit, and added an extra coat of mascara and lip gloss before casually strolling into the bar acting like I’ve never been nervous about anything ever. (key word here is acting) Stan was already there and actually looked exactly like his pictures. (High five Stan!)

Breathing a sigh of relief, I sat down and let him order me a Pellegrino garnished with a lime as he ordered a whiskey on the rocks. I don’t drink alcohol, so this is usually the first thing that will come up in a conversation with someone new, because 97% of the time, when meeting at a bar, they will question why I didn’t order a cocktail or a glass of wine. Thankfully, Stan had good manners and didn’t seem bothered in the slightest about my beverage choice. (You’d be surprised how many dates I’ve been on where a guy just can’t seem to let it go that I don’t want to get boozy with him.)  Score two for Stan! (The first score was the fact he actually looked like his pictures.)

The conversation flows easily and I find myself laughing out loud at his sense of humor. Stan is funny, smart, articulate, and has kind eyes. As the confident gal that I am, I’m asking questions and I am quite pleased at the answers I’m getting back. Time flies by and the next thing I know it’s been a few hours and the current bar we are in is starting to get very “night clubby.” (Yes, that’s an official term) \

Dating in your 40s is tricky sometimes, especially when spending time with someone new. Neither of us were feeling the bar club scene, but we also weren’t quite ready to say goodbye yet. Stan asks if I’d like to move down the block to a sports bar and grab a bite to eat. Why yes Stan, I’d like that very much. After picking up the tab, he puts his hand on the small of my back as we exit the bar. Stan reaches for my hand and a bar hopping we go to the next stop. I’m a sucker for a good hand hold. Smooth move Stan, smooth move. At this point, I’ve lost track of Stan’s score in my head, I just know that I like Stan and I’m having fun.

Relocated at Henry’s, we order some food and I get wild and order a Ginger Ale. We’re exchanging dating war stories, talking about our careers, and I suspect he’s half watching whatever game is on the TV screen that’s behind me slightly above my head. But hey, that’s better than half watching the hot waitress that’s serving us, so I let that one go. The conversation continues to flow and at one point Stan gives me a quick kiss in the cheek. Stan, you sweet little devil you.

It’s now a little after 10pm and we aren’t ready to call it a night, but we’re also a bit tired of sitting in bars. What next Stan? What’s our move? I’m feeling bold and I ask him if he’d like to come over and watch Saturday Night Live at my house. He said he’d love to but it’s hard for him to watch TV with his contacts and would it be ok to swing by his house and get his glasses first.

Now, we’re in Bellevue. I live on Mercer Island, and he lives north up in Mill Creek. I suspect Stan is geographically challenged in addition to being a bit nerdy, yet not nerdy enough to actually be packing a spare pair of eyewear. Mmm, so THIS is dating in your 40s?!?! To make things easy, I offer to go to his house for TV time so he can have the comfort of his glasses. Being the gentleman Stan is, he double checks to make sure I’m comfortable with this decision. “Yes, Stan. I’m fine.” Then I proceed to tell him I’ll be taking my own car, calling a bestie enroute and giving her his address, plus turning on my GPS tracker so she can find me if need be. If this is his moment to kill me and chop me into tiny bits, I explain, he will totally get caught and then I gave him a sly wink.

Fast forward to Stan’s house, we are now comfortably sitting on his couch and waiting for Saturday Night Live to start. I have to tell you, Stan has got his shit together. He owns a beautiful, new, four bedroom, four bath home, drives a brand new BMW 3-Series and seems to have a real affinity for Pier 1 Imports. While I’m not sure why a single guy that’s never been married and has no kids needs a home this large way out in the burbs,  I’m impressed as I am simultaneously bombarded with the smells of Pier 1 Imports Cuban Vanilla room oil diffuser. (Stan REALLY seems to love Pier 1 Imports.)

While we are waiting for SNL to start, nestled into his deep and comfy couch, Stan goes in for the kiss. A real one this time, no more of the kiss on the cheek business. In that moment, I forgive Stan for his obsession with Pier 1 Imports and the fact I think a beaded pillow is scratching the backs of my arms. I mean, I shop there too sometimes, once in awhile. Ok, not really that much, but who am I to judge if he wants every single item in his home to be from that store? There could be worse things Bryson! Stop being Judge Judy!

We start making out a little bit. (Mom & Dad, if you’re reading this, I promise it was a rated PG make out session.) In the midst of our make-out session, I feel my Apple Watch vibrate, which usually indicates I’m getting a phone call, a text,  or the KING 5 app has just sent out an updated news story. I ignore the vibrations as I’m trying to focus on making other vibrations of my own. But it keeps happening. Over and over. Buzz buzz buzz on my wrist. WHO is calling me at almost midnight on a Saturday night? Don’t they know I’m making out?

I give my watch a casual side-eye, only to see that Jennifer, my son’s stepmom (or Mom.2 as I like to call her), is calling. Ohhhh nooooo. That can’t be good. I turn to Stan and call a time-out as I go searching for my iPhone that is buried somewhere deep inside my handbag on the dining room table, somehow already engulfed by Pier 1 Imports placemats, napkins, and decorative napkin rings. In the back of my mind, I start to think, is this house too staged? Why does he have eight place settings out on his dining room table? The strong whiff of the Cuban Vanilla diffuser brings me back to my senses. Must find phone. Must call Jakob. Must make a mental note to make-out more often.

Upon retrieval of my phone, I see I have not just one, but seven missed calls! SEVEN! Two from Jennifer and five from my 21 yr old son Jakob. Ooohhhh great. Something bad has happened. My mind starts racing and I’m making lists in my head of things I don’t want it to be as I hit speed dial and call Jakob back first.

Bubba! What’s the matter?” escapes out of my throat, louder than I was intending. “Don’t worry Mom! I’m almost there!” Oh no. This isn’t good. “Where honey? I didn’t check any of your messages. I just called straight away when I saw all of the missed calls.” (Please don’t say hospital, please don’t say hospital I chant in my head over and over) The phone goes silent.  “Um, Mom. I’m almost to you. I’m a block away. Why are you in Mill Creek?” Insert DJ record screeching sounds here. GASP!!! Wait. What?

Jakob, WHY? What do you mean you’re almost to me?” I am so confused as I glance over at Stan, who is pretending to watch SNL, but I can tell he’s really just listening to me. When my son is mildly frustrated with me, his voice will get very, very calm and he will speak slowly with intention. Mom, you sent me a 911 SOS text message with your GPS location. Are you ok?”

Insert backstory here. I have a heart condition. Three years ago, I had emergency heart surgery. My LAD, also known as the widow maker, was 95% of the way blocked due to long term stress and likely consequences catching up to me from my 20s. I went in for a stress test only to fail it miserably and be rolled into surgery a few hours later. It was a real shocker, because no one saw that coming, not even the cardiologist I’d been referred to after two rounds with the ER for weird, flu like symptoms and a strange feeling in my chest I couldn’t explain. My blood pressure and cholesterol were totally fine, and everyone thought I was simply having anxiety or panic attacks.  While I have been given a clean bill of heart health now, it was a stressful time for both me and my son. After that summer, I not only bought myself an Apple Watch to monitor my heart rate, but I also completely filled out every detail in my Health App, including a robust emergency contact list.

Fun fact! Did you know if you push the side button on your Apple Watch 5 times really fast in a row, it will send a 911 SOS text message to ALL of your emergency contacts, along with your GPS location? Well, apparently, that can also happen when you’re making out!!!

And that’s not all, it also calls the real 911. I was catching up to speed real fast as I instructed Jakob to abort mission. ABORT! ABORT! I hear laughing coming from the other people in his car, which included his girlfriend Shay, his bestie McCabe, and his cousin Emma. “Uh Mom…are you on a date?” OH EM GEE. I quietly repeat, “Jakob, I am fine. I will call you on my way home. I’m hanging up now.” They had all been bowling nearby in Bothell and apparently raced out of the bowling alley, almost forgetting to take their bowling shoes off, thinking I was having a heart attack. As I hang up, I hear the roaring of their laughter at epic proportions. I really love this particular crew of young adults, just not right now.

Quickly scanning my phone, I see that the SOS 911 message with GPS location has been sent to Jakob, Jennifer step-mom.2 (shoot, I still need to call her back), my dad, my mom, my sister on the east coast, and two of my besties Kristin and Erin. Swiftly, I craft a text message that can easily be copied and pasted to everyone explaining I was fine and there was some weird glitch with my Apple Watch. No need to worry. Nothing to see hear. Move along please!

Mid frantic text messaging, the real 911 calls to see if I’m ok. For. The. Love. I look over and see that Stan does not seem to be amused, nor is he watching SNL. I’ve now been on the phone for what feels like 100 years. Please dear God, make it stop.

Once my situation is somewhat back in control, I set my iPhone down and I turn to Stan, who is still just staring at me like I have two heads and one really, really red face. This. Is. So. Embarrassing. Stan asks if everything is ok and I try to explain what has happened, even though I don’t 100% really understand how this has happened. Listening intently, Stan asks “Um, are the cops going to show up here?” I’m now wishing the embroidered couch pillows from Pier 1 Imports would open up and swallow me whole, scratches and all. How on earth did we go from watching SNL to acting out one of the real-life comedy skits you might see in the show?

I take a really deep breath as I thank Stan for a lovely time, explaining that I think our date has peaked and while it’s been memorable, it is in fact time to call it a night. Stan slowly states with a blank face “You know, if you weren’t comfortable coming over, we could have gone to your house or just scheduled a 2nd date. I asked if you were going to be comfortable.” Trying not to yell at Stan that this is his fault for having poor eyewear selection earlier in the evening, I sweetly explain that clearly the problem was that I got entirely too comfortable, and it was time to go. Looking perplexed, he says “I have to ask. Do you find yourself in these types of situations often?

Yes, Stan. I do. Maybe I shouldn’t have told him that story of the one time I fell backwards through a foam core step & repeat photo wall at fashion week. Did he really need to know that I’ve been pooped on by a bird three times in my life and one of those times was at Disneyland? (Happiest place on earth my ass!) I could almost see him trying to swipe left while looking at me in hopes I might just disappear in a poof of smoke. Putting on my biggest IDGAF smile, I thanked him again for a memorable night and said if he’d like to get together again, he has my number.

I call Jennifer, my son’s mother of his other brother, on the way home and start explaining what happened. Before I’m even half way home, we are laughing so hard that tears are streaming down my face and I’m trying really hard not to pee my pants. Jennifer is shrieking with laughter as she exclaims this could only happen to me. And if you know me, then you know she is 100% right. Stan did call the next day and we did go out one more time. I left my Apple Watch at home for that one.

While it’s starting to feel like I may be single forever, one thing is for certain. There will be no dull single moments for this gal in this lifetime. In the words of Carrie Bradshaw, “Eventually all the pieces fall into place. Until then, laugh at the confusion, live for the moment, and know that everything happens for a reason.” 

Perhaps the gem that I will take away from this silly little story, is that when my son thinks it really matters, he drops everything, races out of a bowling alley to save me and shows up for me with his posse in tow. And that, my friends, is the kind of love that makes it just a little bit easier to be a single gal in the city.

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