My Top 3 Most Awkward First Date Moments

I’m a bit of a perfectionist.

Dating was important to me from a fairly young age, because I thought that being in love would fix all of my problems, from my glaring emotional insecurities to why pants never fit me right. So when the time came around for me to date, I wanted to do it correctly.

The problem was that I was growing up during the dawn of the internet and a golden age of romantic comedies, and while young me hoped this would provide answers, it only created a crowded and ambiguous thought bubble full of questions. Questions that I still have to this very day.

And so, here we are.


From my pre-teen years onward, I always thought it was kind of weird that men were expected to pay for everything on dates, based on what I had observed and read. I understood where the idea came from, but now that we were living in a time in which women earned their own money and forged their own independent paths, it didn’t make sense to me. I also feel horribly uncomfortable whenever anyone does anything for me. If I ever broke my leg, I would still limp my way to the kitchen for a glass of water to avoid inconveniencing anyone.

Of course as an uptight, angry teen, I thought the idea of a woman paying was highly progressive and that my cause would contribute to the betterment of humanity. To the point that I was pretty militant about it. Any guy who offered to pay got a hard no (it, of course, never occurred to me that the money I spent usually came from my father’s wallet since I had no pennies to speak of at the time).

When I was about 19, I was talking to an ex-boyfriend and he casually mentioned that while he supported my viewpoint, if someone wants to treat you, sometimes it’s polite to just let them treat you. So when another guy pulled up to my house for our first date, saying he was going to treat me to miniature golf, I decided I was going to try and be treated. What could be so bad about a treat?

When we arrived at the mini golf course, I started to panic. The idea of letting him pay made me feel so…dependent, powerless, weak. I was coming around to understanding that’s not always how the treat-er sees it, but the helplessness that started to take over my body was uncomfortable and making me feel sick. So when he was about to walk over to pay for our mini golf outing, I knew it was going to happen.

But that didn’t mean I had to see it happen.

“I…uh….” I stammered.

“You okay?”

“Yeah, all good, I just uh…” Think, Jillian, think! What is a good excuse? His beautiful face is staring, waiting.

“I’m just…gonna stand over here.” Yes, that makes sense.


“I’m just gonna stand over here for a minute.”

“Do you need me to…stay with you?”

“No! No…that’s alright. You go over there. I’m just gonna stay here.”

He raised one eyebrow at me, but he did listen. And he did date me for a little while after this. Bless him.

I then proceeded to hide behind the bathroom building and let the transaction happen at a distance.

It occurs to me all these years later that I could have just said I had to go to the bathroom. That’s probably a more normal thing to do, right? Oh, well.


Because I, like many, was a walking bucket of contradictions (still am, just different contradictions), even though I felt I was pursuing a great feminist plight financially, I also still really wanted boys to like me. This combined with a total lack of social and self-awareness at the time really made some weird science happen.

I used to be a lot more preoccupied with physical appearance than I am now. I think being healthy and feeling your best is important, but back in my teenage years, my warped brain was downright obsessed with keeping my weight low and making sure nobody knew that I ate.

Which proved tough. Because I can eat, friends. Like, really eat. I have no sense of fullness. Only a sense of sickness and self-loathing.

But I thought that showing off this talent would be unattractive to the opposite sex. This started to be a sort of problem when I entered the “getting asked to dinner” phase.

Once for a first date, a guy took me to a nice pub with a small menu, mostly consisting of burgers, wings, and other messy foods that I could chew loudly and get all over myself as I licked the plate clean. Also, he had already said he insisted on paying, and if I was going to allow that, you could bet your arse I was going to get something real cheap. I perused the menu for something that would make me seem dainty and low-maintenance (even though I am neither). I settled on a stuffed mushroom appetizer, knowing how impressed he’d be by my teensy appetite.

“Are you sure that’s what you want for your meal?” The waiter asked. “It’s kind of small.”

“Oh, yes, that sounds perfect,” I responded as my stomach growled at me.

“You girls always eat like birds,” my date said through a small smile (see! It wasn’t just me! We all had them fooled).

Turns out “kind of small” meant one mushroom, stuffed with breadcrumbs and cheese, in the middle of a white plate.

Now I didn’t want to eat too quickly and appear gluttonous or make him feel like he had to eat his actual, normal meal quickly, so I decided to cut the mushroom into crumb-size pieces, fit for the delicate birdie-ness I was emanating, and ate them at a very slow, calculated pace. I think I actually finished after he did.

Then I went home and made myself nachos and he never called me again.


This story, while awkward, is also about effective techniques one can adopt in the face of douchery. It is about survival.

I went on a first date and it was going well. Pretty low-pressure stuff: fruit smoothies, a walk around town. He seemed nice.

Of course it turned out, for this man, a date that’s going well means he’s totes gonna get laid after.

So, as we pulled into my driveway, I leaned in to give him a tame kiss on the lips, and he took my face in his hands and forced my mouth open with his tongue. I pulled myself away because, ew, gross.

“What are you doing?”

“You, hopefully,” he responded with a smugness so potent, I wanted to throw acid on it.

He started leaning in again. His face was mere centimeters from mine.



Then I jumped out of the car and ran.


No, I Don’t Want to Make Out with You (and Other Social Faux-Pas)

Whenever I’m at some sort of gathering of my peers, I usually have my Awkward Sensors on. It’s not always intentional, but I’m generally able to sniff out those who are just as uncomfortable as I am. And then we sit next to each other in eye-contactless silence and a new friendship blossoms.

But sometimes there is that person who clearly wants to be included, but other people are avoiding them because they’re hard to talk to or maybe a bit unpleasant. And I inevitably end up talking to that person because my empathy kicks in (I’m fairly certain I’ve been that person before) and because sometimes I prefer a little genuine unpleasantness to forced conversations about nothing.

But sometimes that comes back to take a big ol’ bite out of my behind. Because sometimes that person reads your talking to them as you wanting to hop on for a ride.

Perhaps I’m a bit naïve but I’ve never understood why talking to someone of the opposite sex when there is alcohol involved means you are randy and ready for their sweet, sweet love. That sounds like a case where I would avoid talking to that person at all costs.

So, I was at this party and wasn’t really having that great of a time, but I had promised myself I would stay for at least an hour, because this was one of several parties I had been to thus far that summer and had never lasted very long at any of them. Frankly, many people there had no idea who I was. I was hired two weeks into this summer theatre festival to do admin work and not only was everyone else on a different schedule, but I also have this habit of never introducing myself to anyone ever, in the hopes that makes them less likely to remember what it’s like to watch me eat.

Anyway, there was this guy there who I had spoken to a few times. He was a bit of a narcissist who made people feel uneasy, but he wasn’t the worst person I’d ever met in my life. We all have our flaws, and he was clearly looking for someone to hang out with, so I thought I’d go over and chat. We talked about things I like to talk about (books, mostly), and repeatedly, people would walk behind them so they could shake their head at me and make a “What are you doing?” face, and I would roll my eyes. I was getting texts from someone else I knew at the party saying, “Are you INTO him?” And no, I wasn’t. I was honestly just trying to be nice, so that when I meet St. Peter at the pearly gates, our encounter would be less awkward.

It was getting late and I wanted to leave. He asked if I would like to take a walk. We were all living on a college campus and I was planning on walking back to the dorm I was living in, so I said sure. Little did I know this was some sort of secret code for a booty call request. Now if a guy asks me if I want to take a walk, I just slap him in the face and run.

We got about a few feet from the party before he pulled me into him and said, “I’d like to kiss you, may I?”

“Uhhhh, no, thank you,” I responded.

He frowned and furrowed his brow, but he let go of me and we kept walking.

He fell in step behind me and I thought maybe, since everything was super duper uncomfortable now, he was just letting me go ahead and ending it there. For that, I would have been grateful. However…

Suddenly, there was a pair of hands on my shoulders. His thumbs were digging hard into my spine and I thought…this is it. He must know some pressure point in the spine that will knock me unconscious and then he will smooch me to death and bury my body. This is how I die.

Then he moved his thumbs outward toward my arms in a light, stroking motion.

He was massaging me. While we were walking. A mobile massage.

Well, this was a first.

“What are you—?”

“Shhhhhh,” he said, running his fingers up my neck and to my ear lobes, “don’t ruin it.”

I opened my mouth to say something anyway, but then there were two fingers in my ears. In my ears. Moving in a circular motion, rubbing my hearing holes. All I could think was, walk faster, Jillian, but it’s very hard to walk faster when someone else’s fingers are in your ears.

We were only a few feet away from the dorm at this point. My keys were in my hand and I was ready to get the fuck out of there. As we reached the door to my room and his fingers came out of my ears, I felt a beautiful Hallelujah envelop me in a warm hug.

“Well, goodnight.”

“Mind if I come in?” He asked, keeping about two whole inches of space between us.

“I’m really tired.”

“Just for a minute.” He pushed himself into the room. I made a point to leave the door wide open. Now, I’ll admit, I was a bit scared.

He pulled me into him and tried to place his mouth on my mouth. I tucked my lips so far into my mouth that they hopefully wouldn’t be back until it was time to announce it’s spring. He was biting at them, trying to get at them, chewing on my chin like a corn cob.

I pushed him away. “I’m cold,” I said abruptly, moving to the heater on the opposite side of the room.

“You know what keeps people warm? Blankets.” He started making his way over to the bed. I took him by the shoulders and pushed him toward the door. But he looked a little turned on by this. So I did the only thing I could think to do.

“You know what else keeps people warm? Calisthenics.” And I broke out into a set of jumping jacks.

It is the first and only time I have heard of anyone using jumping jacks to get out of awkward making out. Patent pending.

He frowned and furrowed again. “I get it. You’re not in the mood.”

Gee, ya think?

He finally left after that. I shut the door, locked it, and sat on my bed for awhile, pondering every moment of my life that had led to a somewhat-acquaintance giving me an ear massage.

The next morning, more texts came in. “Did you guys hook up?” “He said you hooked up.” Ugh.

As ridiculous as this night was and as good an anecdote as this has become, I consider myself extremely lucky and learned a lot from the experience: don’t leave a party with a dude you barely know, don’t assume people are into the conversations they are having or the people they are having them with, if you’re walking with someone carrying obvious tension in their shoulders, maybe you should try backing off instead of on, and cardio, man. Cardio saves mouths.


The Weirdest Guy I Ever Sort of Dated

Perhaps I am digging myself in a hole by bringing up this guy this early in my blogging career, but I was thinking about him recently (because I think he’s engaged or something. Just goes to show there’s someone for everyone!), and decided it was a story that I wanted to tell. Fret not, fellow awkward-teers! I still have plenty more material.

He was a friend of a friend and he was very cute. He also appeared to be just as awkward and as terrible at flirting as I was, so we hit it off pretty quickly. We used to kick each other and toss out harsh insults because, even though I was 20, expressing my feelings made me just as uncomfortable as it would the average 12-year-old boy. I thought he had a similar strategy for obtaining someone’s love and trust. I later came to learn he was instead the quintessence of an “odd duck” and no better at life than a smelly, old douche.

The first incident of overt weirdness (IOW) was when he asked me to eat breakfast with him one morning before class. We agreed to meet up at 8:45. So, I got there at 8:45 because there is absolutely nothing exciting about me. It was very clear he wasn’t there yet, since there only about 3 other college students who regularly ate breakfast before 10. I got an omelet and I waited.

I am not good at waiting because I automatically assume the worst. When 9:10 ticked by, I began to realize that I hadn’t been asked out for a romantic cafeteria breakfast for 2. I had been led into a trap. I immediately began looking around for a clever place to hide a paintball gun sniper or a bucket of pig’s blood, when I saw him strolling in around 9:15. We had class at 9:30. He looked right at me but didn’t acknowledge me, bought a granola bar, sat down without saying a word, opened the granola bar, took a bite out of it, then looked at my plate and said, “Whoa, big omelet!” (It was a big omelet. I was hungry again 30 minutes later. When am I going to stop this silly writing business and realize competitive eating is my calling?!?!).

I said nothing in response because I was confused. He finished his granola bar, looked at his watch, and said, “Well, time to go. Can we do this again on Thursday?”

…Sure. I could eat alone again on Thursday. In fact, I was looking forward to it!

Thursday rolled around and I trudged into the cafeteria at 8:45 to enjoy solitary meal of silent solitude. I got another omelet and sat down at a small table-for-two. The guy was nowhere in sight. I chewed with my mouth open and got ketchup on my shirt because 8:45 me doesn’t give a shit.

I looked up to assess my surroundings because I would probably choke if I didn’t slow down when I saw him sitting a few tables away with some other guy. We made eye contact and he waved. But what did it mean? Was it a, “Hey, there you are! Come over here!” wave or a, “Oh, God. She sees me. Better be friendly or she’ll eat me next,” wave. I had no way of knowing. So I just sat there and kept staring at him for awhile. Probably muttering all these thoughts aloud with a twitching eye.

He waved again, unfazed, which led me to believe that yes, I was supposed to go over there. I sat down and he said, “I’m so glad you made it. This is Eric.” Eric and I exchanged our hellos, and then he and Eric continued to talk as though I wasn’t there. 9:20 came along and I announced I had to go. He looked up at me with an adorable smile and said, “You have ketchup on your face.”

My natural assumption was that I had been friend zoned. And I wasn’t too broken up about it, to say the least.

One night, my friends and I decided to go to a party in one of the on-campus apartments. So they got all dolled up and I left my day clothes on and followed begrudgingly behind them because I need a barrier between me and the people at all times. The party itself wasn’t that bad as far as parties went. We were dancing and having an okay-enough time when I got a text from the guy that said, “Where are you?” Hmmm…odd. Especially with no context or prompt. Why was he looking for me? Was I the rook is some greater government scheme after all?

I texted him back my exact location and I swear, not 10 seconds later, he burst through the back door with the force of a sassy, drunk giant. He walked straight to me, eyes only focused on me, pulled me into him…

And we started doing about the most awkward dancing that any two already-awkward people in this world could accomplish. It was some uncoordinated combination between traditional salsa, the percolator, and two paraplegics trying to hold each other up. His mouth was open and he was slobbering on me like a horny dog. It was magical.

He came back to my dorm with my roommate and me. She managed to fall asleep despite the fact that he insisted on continuing to dance. This time to obscure 80s Irish music (yes, you read that correctly). He had my wrists in his hands and he was swinging them back and forth with utter fascination, he was looking at me longingly, and so I took that as an opportunity to lean in and kiss him.

It went on for a little bit. He was a surprisingly good kisser. But suddenly, he pushed me away and said, “I like cheek kisses better,” and planted a nice wet one on me. Hey now, what? I mean I had showered that day and my breath probably smelled like peach schnapps. I was a breathing, passably attractive female standing in front of a 20-year-old man and he wanted cheek kisses? IS IT CUTE OR IS IT CREEPY, READERS?!

These weren’t nice little cheek pecks either. He was voraciously kissing my cheek. He was kissing my cheek with passion and fervor. He was making out with my cheek. Now I was starting to get concerned.

“Can I sleep here?” He asked when he finally came up for air.

“Uh…..” (I go over how I feel about sleepovers in Spending the Night: A Tragicomedy).

“I just want to sleep next to you.”

“I mean, okay.”

So we climbed onto my top bunk and laid down. I turned one way thinking he’d want to spoon me or something. He turned the other way and went to sleep.

The next weekend, some friends were visiting my roommate and me from another college. The guy and I had been texting all week and actually ate breakfast alone together and I was getting kind of used to the cheek kissing, I guess, so I asked him to come over and hang out with all of us. He stumbled into my room, perhaps the drunkest I’ve ever seen a person, saw my black friend, and immediately started spurting out some of the most racist things I’ve ever heard. He was an awkward, skinny Catholic racist. He was the boy who couldn’t say a word to me over a granola bar and here he was casually throwing around deeply offensive racial slurs. I had to get him out of there before they all kicked his ass.

He asked me to go back to his room to “read his novella.” This was not a euphemism. This is actually what he wanted to do. Only when we got to his room, he decided he didn’t want me to read it because the story was too nice. So we sat on the floor across from each other in the pitch dark for awhile because he didn’t want to turn the lights on, when he leaned toward me. I thought he was going in for one of his special cheek kisses and braced myself, but instead he whispered in my ear, “Can I tell you a secret about me that nobody else in the entire world knows?”

Well, what are you supposed to say to that other than, “Okay”?

He leaned back and stood up and turned to stare at his wardrobe as though he were a mad scientist staring at his most grand experiment.

“I love to shop,” he said as he bust his wardrobe open with vigor.

And in that wardrobe, lined up and perfectly pressed, were about 50 black V-neck t-shirts. Nothing else.

“I love clothes. I love fashion. I love looking good,” he sighed and sat back down. “So, that’s me.”

I nodded.

We sat there in the dark silence for a bit longer after that and I guess at some point, I fell asleep on his floor. I rushed out the next morning before he woke up, but freaking Eric saw me leaving his room, and then there were rumors for awhile that that guy had finally gotten laid. I didn’t bother to correct them because first of all, I didn’t care. Secondly, who would believe the real story?

There are a few other IOWs from this period of my life when this very strange individual and I were cheek canoodling, including one that involved a pizza party and a suspicious encounter with one of my professors, but this is most certainly the highlight reel. We didn’t talk much after that. Maybe telling me his deep, dark secret took too much out of him. Suffice it to say, my cheeks were grateful.

The Top 5 Most Awkward Kissing Techniques

Kissing is one of the few dating-related categories I like to think I understand. Whilst a good ol’ fashioned lip-wrestling match can be intimidating, there are certain go-tos one can always abide by: 1) Kissing is defined as the touch of the lips as a sign of love, sexual desire, reverence, or greeting. Take note of the word “lips.” Your lips are the samurai, the tongue is merely your sword. 2) If you get bored, tilt your head. You may appreciate things from another angle. 3) When in doubt, follow the leader. Remember, everyone has spent time and energy refining their kissing manners. Whatever they do to you may very well be what they expect from you, so it is perfectly acceptable, when you’re at a loss, to just do what they do.

Unless they do one of these things.

5) The Swash Buckler: Argh, yer matey’s vessel has apparently hit rocky waters. Consequently, they feel they can only open their mouth partially so as not to take on too much water, and their tongue is going to swiftly move back and forth to counter the rhythm of the waves. This technique will leave you with few places to go. The quick, yet predictable movement of the tongue makes it hard to add variety, and the semi-closed mouth means you’re just going to taste whatever’s leftover from their dinner.

4) The Face-Eater: A face-eater understands the importance of the lips within the kissing context, and I commend them for it. Face-eaters are potentially solid kissers who don’t understand the scope of their mouth size. So their whole mouth ends up encapsulating your whole mouth and they’re essentially making out with your nostrils and chin, leaving you to feel like you’re being swallowed by a slobber whale and likely unable to breathe.

3) The Chomper: Lips are friends, not food. If your tongue is your samurai sword, then your teeth are your firearms, only to be taken out when you know you’re at war. A little light, playful biting never hurt anyone, but for goodness’s sake, buy some Trident if you’re looking to chew on something.

2) The Fire Stoker: When your partner doesn’t feel your mouth is open wide enough, sometimes they may feel compelled to stick their tongue tonsil-deep in your mouth repeatedly until they achieve the circumference they desire. Not only is this a choking hazard, it may cause spit to spread rapidly. Do not try at home. Do not try ever.

And, tongue-roll, please…

1) The Combination: Every so often, you may be blessed with the opportunity to make out with someone who can simultaneously achieve all four of the above. I have on two occasions. Remember, this is a privilege, not a right. Embrace it. Learn from it. (Also, when referring to this technique in casual conversation, remember to sound as French as possible. Otherwise, let us not go to number 1. ‘Tis a silly place.)

None of these are a deal-breaker for me, of course. Any beast can be tamed. But the most important thing is that you find someone whose awkward kiss matches your awkward kiss so you can fall in awkward love and spread the Book of Awkward.

Did I miss anything? Got a kissing horror story? Leave a comment.