Dating, It's Complicated

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Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


My boyfriend has taken a liking to talking like a robot occasionally. It was funny, until one night I turned all the lights off, got into bed with him and got super close to him, went in for a kiss and right before we kissed he said, “Chance of intimacy increased to 40%” …in his robot voice.
Tasha

Every time I see my boyfriend he insists on smelling my face and guessing what I last ate. He has never guessed correctly.
Ali B

I don’t know which makes me happier, the fact that I turned my girlfriend into a gamer and fellow lover of Skyrim, or the fact that we have sex to the soundtrack.
Jason D

For a few months now, my boyfriend has been referring to my bras as “boob prisons.” As a result, he frequently campaigns for “boob emancipation.”
N R

| 24 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


The first time I had sex with my boyfriend, and after we were both done, I jumped off him to open the window to cool off and the first thing he said was, ‘That breeze is the best thing I’ve ever felt…’ Wow
Dani S

I’ve got a bit of a unibrow, which I never really had a problem with, but my ex-girlfriend really hated it. She hated it so much that she would pin me down and pluck my eyebrows before I could get up for class. I have to admit though, it was kinda hot and I did look better afterwards
A. S.

My totally normal girlfriend somehow became a little bit of a nerd when it comes to humor. Last time I dropped something and my girlfriend started clapping hands and moaning “Owned, Owned, Owned” like a seal. I’m freaked out.
J S

| 28 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


When I am making out with my girlfriend, sometimes I poke my tongue in and out really quickly, one would think it is moment killer, but she giggles for a little bit then we make out more intensely than before, we have termed it “The Gecko”
Rich H

Although my boyfriend and I spend most of our evenings watching movies, the night almost always ends in us having sex. On nights that we watch Lord of the Rings (my favorites, not to be easily interrupted) we play what he calls Mordor- he does absolutely all that he can to open my legs. I have been dancing since I was 5… and I have unbelievably strong legs.

You know what they say: One does not simply walk into Mordor.
Catherine K

| 35 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


After going out for two years my boyfriend has never remembered my birthday, a week ago he told me he would never forget my birthday again, I asked him why? Apparently it’s the same day as the last Batman film. He also made sure to mention he was going to be busy on my next birthday.
Amy R

I’ll be the first to admit that I tend to shy away from all things kinky. My boyfriend gets really enthusiastic when we have sex, and to be frank, I get tired after a while. In order to speed things up, I take top and work him out. He especially likes it when I talk dirty, though it makes me feel like a hooker. Regardless, the fake kinkiness gets him to finish and lets me go to sleep. I’m a horrible person.
F L

Every time my shirt is off in front of my boyfriend, he always looks at them like a child on Christmas and says, very surprised, “BOOBS!” and then tries to motorboat me.
A B

| 37 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


Two days ago I was lying in bed with my boyfriend. He was lovingly stroking my cheek when he said, in the sweetest voice, “Your side-burns are so cute.”
T

Every now and then, when we’re having sex, my boyfriend will moan his own name and talk dirty to himself.
Jenny S.

My girlfriend is scared—literally scared—of seeing me naked. She has brought herself to tears thinking about my naked body. I don’t know how to take that…
T

In the shower, my boyfriend grabbed stray pieces of my hair and arranged it to look like a stick figure giving another stick figure a blowjob. It was actually pretty artistic.
Ann M.

| 27 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


My girlfriends gets mad when I tell her I’m reading while having lunch. She also gets mad when I don’t read her text messages while having lunch.
J

My wife just got a 2 1/2” haircut. She is now crying.
F L

You know it hasn’t been a very successful semester when you have to dust your box of condoms.
Jace K

I just read the one where the husband says “Okay and dismount” at the end of sex. When I’m on top and we finish up, I always say “Over and out” as I get off of him.
M

| 20 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form.


While snoozing naked in this guy I’m seeing’s bed, he likes to squeeze my butt checks while quoting Bart Simpson. “Hello, I’m Dr. Cheeks. I’m doing my rounds, and, uh, I’m a little behind.”
M

I don’t consider any sex I have with my girlfriend official unless it involves me raspberrying her boobs.
C

The guy I am secretly in love with told me that I was “good breeding stock.” I don’t know how to take that.
Carly

My left boob is a bit smaller then my right one so my boyfriend decided to name them Serena and Venus…
AA aa

| 23 comments
CH Staff


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic “submission form”:/submit/dating-its-complicated/.

My girlfriend broke up with me for 2 weeks because she found out I was cheating in Words with Friends…
Ryan P

I took my ex-girlfriend of three years to a pretty cool noodle bar, spontaneously (as she always complained I wasn’t spontaneous enough). She wouldn’t speak to me when the main meal arrived or for two days afterwards. Apparently according to her, my intention was to humiliate her – because she has never used chopsticks before.
Vince Sal from University of Leeds

I asked my boyfriend to say something nice to me. He responded by saying he likes the way my neck muscles bulge out when I turn my head to the side. ..Thanks?
A B

| 35 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!

My girlfriend likes to pretend that her breasts are defibrillator paddles and proceeds to yell, “CLEAR,” then jolt me with her naked chest. Can’t say that I am complaining.
Barry M

After a very sweaty session in bed, my girlfriend and I spent more time on laughing and making farting noises by pressing together our sweat-ridden stomachs than actual sex.
A

My boyfriend really loves boobs, and has recently decided that he must make the Dr. Zoidberg “Woopwoopwoopwoop!” noise while playing with mine.
R M

| 45 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!

I told my girlfriend she looked like Jessica Alba, thinking it would be a compliment. She said, “Ew, you think I’m ugly?!” She then showed me non-flattering pictures of what Jessica Alba looks like without makeup online.
Ian

So I was having a shower with my girlfriend the other day, and right in the middle of the shower a big snot bubble comes out of her nose as she tries to kiss me.
Dan C

My girlfriend has an iPhone and I always bug her that my phone is better. We were looking at a map on my android phone and I told my girlfriend that it even tells you direction and time for driving and walking. Then she looks at the 4 icons (driving, transit, bike, walking) and says, “What if you were on a motorbike?” I was like o_o?
Kam N

| 22 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


My left breast is a little bit bigger than my right. My boyfriend has named them and taken to referring to them as “lefty and the runt.”
J K

I got rejected by a woman the other night…She Google Earthed my address, saw that I lived in a crappy apartment, and called the date off.
Z R

While I was home for my once a month weekend visit, my girlfriend broke up with me via text message…she lives three houses down from mine.
Brad H

My girlfriend doesn’t like bacon. I like her a lot, but I don’t know how much longer we’re going to last…
Joe F

| 48 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


The night of Homecoming, I went to a mixer between my sorority sisters and a fraternity. I ended up clicking with a guy, playing jenga for hours, then finally getting down to the dirty as the sun rose. We passed out and woke up at noon, just in time for all his fraternity brothers to start rising and making breakfast. I had no choice but to walk through the kitchen wearing last night’s clothing. He walked me out but I definitely heard his round of applause as he headed back inside. On the upside, he asked to see me again.
Melissa F

One time my wife and I were watching TV when a commercial came on for a restaurant, showing food and what not. She gets a big grin on her face looks at me and says, “Wow, that smells so good!”
Michael B

| 46 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


I stayed with my high school girlfriend for two years waiting for her to come to the same college. After she finally comes to the school she breaks up with me within the first month.
Justin S

So my ex used to have a habit of biting her nails. One time during a pretty intense make-out session I started to choke on one of her prechewed fingernails…. make-out session over
J

My boyfriend’s pet name for me is Zergling.
Rachel Hiebert

I read Dating, It’s Complicated: Issue #111 and told my girlfriend about it and now she refers to her period as “shark week” on a regular basis.
Chaz Broseidon

| 45 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


My ex dumped me because “she was getting too clingy.”
Kris

My girlfriend likes to “fluff” and then go “grazing” on my chest hair.
M S

My girlfriend thought that ultra-violet light was actually called “ultra-violent” light because, well, you know, it gives you sunburns and skin cancer.
Alex B

My girlfriend broke up with me when she found out I had sex with my ex before we started going out.
Gregory

My boyfriend likes to pluck my eyebrows.
Kate T.

| 28 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


My girlfriend uses her farts to keep me out of the bathroom while she does her hair and make up.
M J

My girlfriend pronounces pronunciation as “pronounciation.” I’ve never corrected her because I like the irony of it.
Ian S

One day I was with a friend driving to pick up a broken computer so I could fix it when my gf called me, we talked like usual and I started to annoy her playfully when she stated “Oh don’t you start Andrew, I’ll kill you!” where I just had to ask, “Oh? How would you kill me” to which she replied without skipping a beat, “Oh probably with a machete”…..
Drew T

| 43 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!

My boyfriend picked me up at my house one day so I could run errands with him. When I answered the door he gave me an enormous hug and told me that my hair smelled amazing. I thanked him and told him I had just changed shampoo. He said, “Thank God. Your hair normally stinks around this time of day.” I don’t think I’ve ever been more offended.
Maggie K

After reading an article about the possibility of male lactation, my boyfriend won’t let me suck on his nipples during foreplay because he’s afraid it’ll make him start lactating.
L

I met my girlfriend’s dad this weekend and I completely blanked on his name, First and last… there was no Mr. ____ option
Tim H

| 47 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


Today, my girlfriend asked me if my grandmother had any children…
Rodney P

When me and my boyfriend are having sex, I just plan everything we are going to do afterwards.
Selena I

My boyfriend was very reluctant about doing it with his parents being home, because he had a feeling they will, ‘‘know what’s going on.” A while ago, we decided to do it anyway. He discretely locked the door and we started it. As I was going down on him, his cat decided she wants to ‘‘visit us’‘ so she was meowing loudly in front of the door. Normally, he would let her in instantly. The weird thing is, the cat did not stop and started meowing hysterically, so his mother tried to calm her down saying: “Come here, you can’t go there right now! They are busy!” We haven’t done anything unless we were alone since then.
Sandra

| 41 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!

Whenever I take time to pack my luggage carefully, my boyfriend starts playing a loop of the Tetris melody on his cellphone.
Joanna R

My long distance girlfriend makes me shave before we skype.
Ricky T

My husband and I were in Target today when we ran into one of my mother’s friends, who asked if I was feeling better, and when I was due. I’d been feeling ill due to the pregnancy, and it was sweet of her to ask. My husband answered, “She’s due February 12th.” I looked at him, asking, “WHAT?! My due date is February 10th! Why would you think it was February 12th?” My husband argued with me for a good two minutes that I must be wrong about my due date, and then, it dawned on him… “Oh yeah, oops, February 12th is the date that the Star Wars movies are going to start being re-released in 3D! You know, when important dates are that close together, I get them mixed up!”
Barbara R

| 44 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!

My boyfriend and I were in the middle of foreplay, when he whispered in my ear in a really sexy voice, “what do you want me to do to you?” I replied with a simple “whatever you want.” After a moments pause he said, “well, the laundry room key is on the table, and there’s detergent in the…” that’s when I punched him in the arm.
Mandy Q

My girlfriend finally joined the rest of the technology world and upgraded her phone to a new Droid. She became addicted and was showing me all the things that it could do that I obviously knew because i have a damn droid. She finds the Maps feature that shows your current location on a map. Excitedly she says, “look it shows me where my phone is in case i lose it!” To which I reply, “what if you lose your phone?” and she actually said, “I can look to see where it is on here!”
Erik H

| 34 comments
Jason


Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!


My boyfriend refers to my period as “Shark Week.”
A

I went down on my then girlfriend. We had done it a few times so I figured we would be fairly comfortable. So I when I was eating her out I decided it’d be funny to go “Nom, Nom, Nom.”
She wouldn’t let me touch her for two weeks….
Dakota S

Me and my ex-girlfriend were sat in a restaurant with a load of my friends and so we ordered a big platter to share. It comes out and my ex picks up one of the buffalo wings and goes “Wait, did all these wings come from one buffalo?…”
Dylan M

| 36 comments