27 Men And Women Share Exactly What Made Their First Kiss Awkward, Sweet, Or Hilarious

1. Her Lips Were So Soft

When I was 14, I got my first girlfriend. She was really pretty, subtly rebellious, and came from a very close and conservative Catholic family. These were the days when our moms had to drive us to each others’ houses, so the thought of any time alone with her was mind shattering for my balls-deep-in-puberty self. One rainy afternoon after a marching band rehearsal, we walked the two block trek to my parents’ house to watch a movie. In case you are unfamiliar with awkward teenage dating protocol, the movie watching process goes as such: Sit very close to each other, but not quite touching, for at least the first 20 minutes of the movie. No actual movie watching is done during this time; all mental capacity is fixated on how to proceed to step 2. You figure out some way to slip your arm around her despite your only model being the “yawn and reach” from every shitty sitcom ever. If she accepts and leans into you, proceed to step 3.

At least an hour into the movie, you both somehow end up “lie-down cuddling,” an act that would inspire condemnation from her conservative parents. This time is spent desperately hiding your hard-on. The kiss. It is best to wait for a tender point in the movie. However, if you’re an idiot like me and picked “Fiddler on the Roof,” just go for it whenever the Jews aren’t being persecuted. So yes, I went in for it by way of kissing her forehead first. She tilted her head up and our lips met. I kissed her through a triumphant smile, celebrating my victorious rite of passage. Her lips were so soft that I swore I could hear a romantic cello solo unfold out of thin air.

Unfortunately, the sound was actually the civil defense siren warning the town of an approaching tornado-producing storm. Needless to say, I had my hands deep in my pockets the entire time we took shelter in the basement with my parents.


2. Nineteen And Never Been Kissed

I didn’t kiss anyone until I was 19, which he thought was hilarious but cute. We went up to the top of the valley I live in to look out over the city. It was the day after New Year’s so we were talking about what we had done to celebrate and how neither of us had had a New Years kiss when someone started setting off fireworks below us. He had also missed out on fireworks because of a fire warning where he was, so he said something about his New Years being nearly complete now except for one thing, kissed me, and then asked me to be his girlfriend. I said yes!

He turned out to be a cheating asshole, but that night was pretty incredible at the time.


3. Just Under The Surface

It was like 7th grade, and we had been “dating” for like 2 months. Well anyways, we were both nervous as FUCK about kissing, no idea why. Anyways, we didn’t want anybody to see it so at summer camp when we were swimming we both went underwater and kissed. We both emerged cheering and hugging, shit was so cash.


4. Sloppy And Being Watched

I was constantly dared to kiss this one girl who lived two doors down from me. It was really awkward cos my friends wanted to watch to make sure we really did it. We were 11 and it was sloppy.

Gotta start somewhere.


5. “Come A Little Closer…”

Was hanging out with friends, my crush had me walk with her to a more secluded area to be away from everyone. I didn’t know what was going on but she said to “Come a little closer…” She kissed me on the lips. 11/12 year me couldn’t believe it, the only thing that could’ve made it better was if it lasted longer.


6. Truth Or Dare

Gave a couple guys some lingering pecks during Truth or Dare. After the game, my friend hooked up with one of them in the living room (where I had planned to spend the night). With nowhere to crash, the other guy offered his bed. So we got in bed, he asked to cuddle, and I obliged. He told me, “I like that you’re not easy…” Uhh, thanks? He asked to kiss me some more. Alright, whatever. After 30 seconds, I had enough, rolled over, and told him to go to bed.


7. “It Was Our Secret”

I was 16.

I’d known the girl for upwards of 10 years at that point. I was her best friend for the longest time, and although we had some rough patches, we were damn near inseparable. We’d had a lot of bouts of whether or not we were into each other, and during the later stages of Sophomore year, we sorta gave things a shot.

To keep needless details out of the story, I started hanging out with her quite a lot after school. I’d never leave the house usually, but she was the one exception. We’d just go to the edge of the neighborhood, sit on a guard rail on one of the dead end streets, and just chat while we looked at the stars. It was an extremely peaceful experience for such an angsty and stressful time that was for me.

Anyways, one time, probably around May, we were just having one of those chats. We didn’t even really try to flirt with each other or anything, it was just much needed quiet time for the two of us, away from everyone else. We talked for maybe an hour or two, and when things started to get pretty dark, we decided it was best to pack up shop and head on our way for the night.

I get up from the guard rail and casually mention how it was chapping my ass. She laughs and asks if a hug would make me feel better. Sure, I’m thinking, why the hell not, hugs are nice and I very rarely am treated to them. Then, she put her arms around me and just went in for the kill.

We probably stood there for 5 to 7 minutes, just… Yeah. Making out, essentially. Her entire body was warm to the touch, I could feel her heart racing, I could feel my legs shaking, and I have the eternal memory of the perfume she was wearing at that moment. It was all magnificent for the first minute or so. But… She just kept going.

Again, it lasted upwards of 5+ minutes, of continuous face-smushing. After about a minute or two, I opened my eyes to see if this showed any signs of stopping. Nope, she was completely entranced in the moment, and I’m just standing there looking around to see if anyone is watching. Moving my eyes back and forth like in a cartoon in hopes that this wouldn’t turn into something too lengthy. But it kept on going. At about the half way point she started to use her tongue.

It was easily the most enjoyable experience of my life, but man, I don’t think your first kiss is supposed to be an extremely lengthy endurance-run. She claimed I was a good kisser, but I wouldn’t particularly know, given that was the only kiss I’ve ever had the liberty of having. Perhaps it was 10 years in the making, and that’s why it was a bit over the top for the moment, but I still get a laugh out of it regardless.

And before anyone asks, no, I didn’t end up dating her anymore. We had our worst rough patch extremely soon after that, the friendship was essentially destroyed. We managed to salvage what we could, but things were never the same. I still have an extreme desire to be with her, she was perhaps the only source of happiness I’d ever found in my life, but y’all know how it is. Wasn’t meant to be. I still stand by her side when I can, continuing to be that best friend she’s ever had, but that kiss is our little secret.


8. smooching at religious school

I have an interesting one. I went to an Islamic school and our classrooms would have little storage rooms between them (small rooms, say 2.5mx2.5m). Anyway, one of the storage rooms was used as a place to store religious books. I think you know where I’m going. My girlfriend at the time – we were 13 – was particularly open to physical contact in the form of hugs and just generally being touchy feely. Me, being a young sheltered pre-pubescent Muslim student, receiving attention from the opposite gender was unknown territory; highly frowned upon but very exciting.

So anyway Islamic was taught as a subject, and depending on the day we would either listen to the religious teacher talk or read some sort of religious text(Quran or religion textbook). This day happened to fall on the day we would have to read. Before and after class, the teacher chooses a few students (maybe 4 or 5) to go and get the books from the storage room and then another few at the end of the lesson to return the books to the storage room. On that day, I and my girlfriend were chosen to return the books at the end of the lesson. Now up until here, we hadn’t done much but just talk all night on MSN(lol) and hug here and there. So here we are in the storage room putting away a large pile of books, the other 2 students had finished and gone and it was just me and her. She turns to me and says ‘do you wanna kiss?’ I was a very shy kid so I was scared we would get seen. Or worse. But then I thought of how awesome it would be to kiss a girl and how I could go tell my friends about it and I said yeah ok and we leaned in and kissed. Held it for about 2 seconds. It was great. And the deed was done. After Islamic class. Surrounded by religious books. A few meters away from the Islamic teacher. Never forgetting that one.


9. A Touch of the flu

I was 14 on my first date ever with a boy I met in band class. We had just seen Beowulf in theaters and his dad and he were driving me home. Very lovely evening. Well, this boy and I were sitting in the backseat and I decided to summon all my courage and kiss him. I leaned over and kissed him, then immediately threw up all over myself.

I had gotten a flu shot the day before.


10. Absolute Magic

Absolute magic. I was 12. My friend had a backyard party. I was dancing with this beautiful blonde girl from school. We kissed while Axl Rose sang Don’t Cry. Afterward, I thought I feel asleep and dreamt it. 25 years later, we still kiss every day.


11. The One That Got Away

High School library. Wasn’t her first kiss but it was mine. For some reason, I made her really nervous, like butterflies in stomach nervous. She had to cover my eyes to make sure I didn’t see. It was cute. Felt weird but good. We went on to date for 5 years. She is the one that got away.


12. Amazing!

Actually magical! Was in what’s called the Rose garden at her school after dancing lessons. It was amazing.


13. It Was…Weird

It was like kissing a fish sucking on my face for five seconds. It was right after school at soccer practice and my boyfriend ran up and gave a quick kiss. I didn’t know it was happening until he had already run off. Looking back it is hilarious. It was my first kiss and it was…weird.


14. Catering Kisses

Seventeen, got drunk with some coworkers at the end of an event, we did catering and ran the bar and we drank as we went, despite being under age, she was 4 years older, fairly attractive redhead, made out loads over the last couple of hours.


15. A Terrible First Kiss Memory For Everyone

It happened when I was 14 on vacation in Turkey. I met 2 girls there, one was 15 and the other one was 13, I was pretty much only interested in the younger one.

We, all three, spent most of the days together at the beach and went to the hotel bar later in the evening. The younger one wasn’t wasn’t allowed to stay out very long from her parents (sad face), but me and the older one usually got pretty drunk.

One night, she walked me to my room afterward (unexpectedly, for my 14-year-old self) started kissing me in front of the door. I was startled, and like I said, I wasn’t into her, only wanted to get with the other girl, so I told her it wasn’t a good idea, and we parted ways, but the first kiss had happened.


16. The Hottest Girl In School

Fucking awesome. I was in grade 6…so 11 years old. Her name was Sarah, the hottest girl in my school. We played lacrosse for the school on Saturday mornings and used to go to the public pool nearby afterward. We frenched for a good 45 minutes to an hour that day. To be honest that may have been the best moment in my life, pound for pound. I remember hearing ‘Heaven is a place on Earth’ the next day (which had just been released) and just recall being filled with the giddiest sensation, like this world of infinite possibility was going to present itself to me.


17. A Journey Of Bristly Self Discovery

I was a middle schooler and, though I didn’t know it yet, very much a lesbian. I “dated” this guy for a week, mostly because my self-esteem was low enough that I was entirely surprised by his attention. He had facial hair. It was vile.


18. …Okay Bro

I was a freshman in high school. I ended up closing my eyes during my first kiss and missing his lips. When I wanted to try again, he said “it’s your loss” and didn’t let me kiss him again. He was a shitty first-boyfriend.


19. A Truck Driver Signals His Approval

I am german but it was more than 17 years ago. I was on a language education vacation (insert your joke about how it didn´t work well with my English skills).

We were under-aged and bought some cheap wine to chill with our group at the beach. On the way back to our host families we lay in the middle of a big, grassy round-a-bout and watched the stars. Then she turned over and gave me a long kiss.

It was pretty romantic if not for the truck driver driving through the round-a-bout seeing us kissing and honking so loud in the middle of the night. We both jumped up and ran home. Damn, this ended way to quick back then.


20. Netflix and Chill

Well I was 16, he was 15, we were watching silicon valley in my basement and cuddling, he’d kissed a lot of people before, so he’d said he wanted me to make the first move (he claimed he was worried about rushing me, but considering he kept trying to get me to sleep with him starting like a week later I’d say he was lying). So I kissed him on the cheek, and then he kept pecking me on the lips till I got annoyed at that, and kinda tackled him. That relationship basically just became us making out till he dumped me for a girl I’m pretty sure he was cheating with. Fun story, he was actually my second bf, my first bf was about 6 months before that (I was 16, he was 18), and had physically run away from me when I leaned in to kiss him, then didn’t answer my texts or calls for over a month….


21. The Moment Was Amazing, but….

I was 15, there was this senior in high school who started talking to me, for the first time it felt like someone was interested in me, the nerdy shy fat girl with the huge glasses and braces, and it felt nice to be on the receiving end of someone’s affection, which I had often seen my more attractive friends get.

He asked me to meet him by the staircase to the roof to talk, and we decided to go up, he stood at one step higher than me and asked me if I had ever kissed anyone before. my heart started beating faster and I tried to say no but somehow I could only shake my head. He leaned down and kissed me softly, with the wettest lips ever. Honestly, he practically drooled in my mouth (which I told him later and we both laughed at it together). But he just wanted someone to make out with and have sex with before he passed out of high school and stopped speaking to me and ignoring me at school within a week or so after that.

The moment felt amazing, but somehow I always look upon it with a tinge of sadness. That it meant a lot to me, but I would never mean anything to him.


22. Under the Turtle

There is a big stone turtle at the playground of my elementary school. During hide and go seek, I crawled under and hid… She crawled under too… I hope my turtle girl is happy wherever she may be.


23. The Gorgeous Senior

I was 16 and the new girl at school and had a serious thing for a gorgeous senior guy who was involved in all of the same extracurriculars as me, was talented in whatever he took an interest in, he was brilliant… you get the picture. Essentially, I considered my chances with him to be very slim, so I was just thrilled that I had so many opportunities to enjoy simply being around him. One day after school, I was sitting next to the parking lot waiting for my ride home when he sat down next to me and struck up a ten-minute conversation about an upcoming performance our drama department had put together and we were involved in. As we were talking, he touched my chin, said something sweet about not doubting my ability to impress the shit out of the audience when the time came and kissed me. Then, he paused for a few seconds and took off to his car and drove away. He ended up telling me a year later that the reason he disappeared so suddenly instead of kissing me a second time was bc he got the sudden strong urge to sneeze and he was convinced that if he stuck around any longer, he was going to end up embarrassing himself by sneezing in my face lol. I ended up marrying this guy, although we both had other relationships before we ended up together for good!


24. Spin The Bottle

I was playing spin the bottle around age 15, and just happened to land on the person I had a huuuuge crush on. I was really shy and I felt like I was way too old to never have kissed anyone, so I was really excited about this.

I slept over at a friend’s house that night and went sleep walking for the first time ever. I guess the excitement of the night was a bit much for my brain. I woke up at 6 am, sitting at the kitchen table with puzzle pieces stuck to my face.


25. Perfect Timing On A Perfect Evening

It was cute. The night was young, just came back from watching a movie and dinner, walking to the bus stop. It was cloudless and warm enough to wear a light jacket, rare for Dublin. I had let slip that I was into him during the dinner.

We held hands while waiting for the bus to come, chatting awkwardly. When the bus was about to come, I asked him if I could kiss him. He teased me a little bit then invited me to kiss him. Naturally, as soon as I did the bus arrived!


26. A Girl Going For It

Senior prom, we were in the back of my friend’s car waiting for the dance to start. We were in the back and she rolled on top of me. It took me a moment to realize what was happening and then we awkwardly made out.


27. Typical

Completely gross and awkward 😂 it was under a tree and sloppy and he tried to get me to touch his wiener. So I left.

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About the author

January Nelson

January Nelson

January Nelson is a writer, editor, and dreamer. She writes about astrology, games, love, relationships, and entertainment. January graduated with an English and Literature degree from Columbia University.