The Winners of the “Life and Times of Tim” Contest

This was one of my favorite contests ever to read the responses for. The contest was to help promote the new HBO series, “The Life and Times of Tim,” a cartoon series about a young man who always seems to find himself in awkward situations. I asked you guys to email me with the most awkward situations you’ve ever been in, and you did not disappoint me. And, listen, choosing the two runners-up was a very difficult task, but choosing the winner was quite easy.

Congratulations to Anthony E., our grand prize winner, who basically put tears (of laughter!) in my eyes with this little story:

Ok, so this guy Paul that I was seeing was having some friends over at his apartment on the 4th of July this past summer. He and I had only known one another for like a week, so I was naturally nervous to meet his friends, but I figured I was going to meet them eventually, so I might as well get it over with. So, he and I are sitting on his couch when the doorbell rings. He gets up and opens the door, and this guy Ameilo and his boyfriend walk in. Ameilo and I had met years earlier and I had a MAJOR crush on him back then. He knew I liked him and shot me down harder than Greg Plitt’s 6pack. Anyway, I said hello and tried to forget about it. Then the doorbell rang, and another 2 guys came in. One of them being this guy that I had spoken to for months about a year earlier. We decided to meet, and after showing up and seeing what he looked like, I ran away and stood him up!. Again, awkward, but I politely said hello. 5 minutes later, doorbell again. This time, one of my ex boyfriends, EXCELLENT. And then the doorbell once more, enter John, a guy that I had been flirting with an pursuing the same time I was talking to Paul. Cant get any worse right? WRONG!

So now, I’m like totally loosing my mind, and people are passing a joint around. Normally, I don’t smoke, but this was a special circumstance, so I took a few hits. All of a sudden, BAM, I gotta poo. Only problem is, the only bathroom in the apartment is within eye (and ear) shot of the living room, where we all were. So being all screwed up in the head from the pot, I take out my cell and text my friend Matt saying “OMG I’m kinda on a date right now and totally have to take a dump!”. 5 minutes later Matt texts me back, asking me why I’m texting him, and that I’m gross. I then realized that the Matt I text wasn’t my friend Matt, instead it was my Ex Matt, the ex that was at the exact same party I was at.

It was a little harder choosing our two runners-up, because I got so many awesome entries, but I finally whittled it down.

First up is Robert N. with this masterpiece:

It’s the summer of 1996 and the love life is not going so well. At work, listening to morning radio, the DJ asks the listeners to call in with the answer to the question, “What movie title best describes your love life?” After a bit of contemplation, I call in with the answer “Less than Zero”. Apparently, the radio station found another, of the opposite sex, with the same answer and decided we would be a good blind date match. As our “reward” a limo would pick us up and we would attend the Hollywood premier of “Emma” followed by a romantic dinner for two. Immediately, I realized we would not be hitting it off this evening. I proceeded to fully deplete the liquor supply of our provided limo. Following an incoherent dinner, I then passed out on the limo ride to our respective homes. I was awoken in my driveway to the feeling of wet pants(unfortunately, not a spilled drink) and the sweet smell of upchuck on my shirt. I crawled into bed and awoke the next day for work. A few male co-workers inquired how my date was, and, being an immature male of 23, proceeded to embellish my “accomplishments” from the previous evening. As I am describing my “exploits” on the radio, broadcast aloud at work, is the morning show host calling my blind date to see if a love connection was made. With the people I had just bragged to about my false endeavors listening, as well as the rest of my work mates, I was fully exposed as a lying, boozing, pants peeing, upchucking pig. 3 months later, on a study abroad semester in Italy, I met my future wife and we have now been together for almost 12 years…from great depths, one can ascend to tremendous heights.

And the other runner-up is Erin S. with this fabulously awkward moment:

27 years old.
Newly single from 3 year relationship.
Living in the city with 4 other girlfriends in similar situations.
Said girls go out on the town.
Meet girlfriend’s brother who looks like Russel Crowe when he’s hot.
Said guy comes home.
Go to bed, make out.
He opens a window. He pees through the screen.
You decide not to sleep with him, pass out.

Wake up and have to fart.
The bed is cornered.
You are amid the only escape route.
You don’t fart, you shart.
Naked.
In bed with your girlfriend’s brother.
Who has to climb over you to get out of the bed.
Even though he peed through your screen, he’s still cute, so there could
have been potential.
Except now, there is no chance. None. It starts to smell.

“Um, I’m naked, so you get up first!” you say.
At which point, he crawls over you as you seductively wrap the shitty
sheets around you.
No one will ever know . . .

Our honorable mentions (LOVED your stories, but, sorry, no prizes) are Erin M., Katie T., Katie H. and Rob V., and their stories are after the jump, if you just need a good laugh today.

Thank you to all who submitted.

Thank you also to HBO for sponsoring the contest, and be sure to tune into The Life and Times of Tim when it premieres, September 28 at 11 pm on HBO.

Erin M:

So my lil’ sis is a water polo phenom who plays and travels constantly. My parents–being the typical over-zealous parents they are–travel to every game.

One day, catching up with my mom, she tells me how my dad throws up the “peace with a little love on the side” at my sister’s water polo games. My dad’s self-claimed invented hand gesture is in fact the peace sign with pinkie extended–the pinkie being the extra “love on the side.” Quite unwittingly, my father believes two in the pink, one in the stink–or THE shocker–is an appropriate celebratory expression for high school girls’ water polo.

I never thought much of this because I never witnessed it in person. Then I hear my dad’s patented celebratory gesture is quickly spreading among my sister’s high school teammates. A salute, if you will, from the team in appreciation for my dad’s strong encouragement. My sister, of course, is mortified–and after explaining–expects me to fix this. Every goal scored, every good play, “peace with a little love on the side” thrusts triumphantly into the air.

So my parents visit me in San Francisco one weekend for their anniversary. Before they go off to dinner I meet up with them for drinks. As we catch up, my little sister’s accomplishments come up… blah blah blah, the standard. Eventually, my mom says, “Oh, Erin, you won’t believe this. Your sister’s friends are giving your dad “peace with a little love on the side.” Practically the whole team does it. How funny is that?” I need to fix this, now. It has gone too far. So I try to be as gentle as I can about this. THEN I come out with it: “Dad, you CAN”T do that anymore. It is really inappropriate. You have to stop.” Of course he asks, “Why?” And really all I can is, “You just have to.” “Why Erin?” “You just have to Dad,” and I leave it at that. So after drinks my parents go to dinner and I go home and email them immediately.
This is the email…verbatim!
“go to….
www.urbandictionary.com
look up The Shocker, or just Shocker I guess.
I am only telling you because I love you.

Erin”

I get a call the next day from my dad. He doesn’t believe this. He is verclempted. He is CONVINCED he made this hand gesture up. He does not believe it is some sexual, or “gynecological” thing. He made it up and that is it. My most awkward moment is breaking to my parents what The Shocker is: the most obscene, crude, somewhat intimate sexual act of love making one could possibly do.

Katie T:

I’ll get straight to the point here. I had a class with this kid, we’ll call him Andy, and we became very close friends. Not sexually close but we hung out a lot. Then after one night of drinking, things went a bit further than intended. To be blunt, Andy and I were, um, fornicating? And really, it had been maybe 2 minutes. Which is why I use fornicating, because we were not making love, or fucking, or having sex. We had literally JUST STARTED. And 2 minutes is pushing it. All of a sudden, he THROWS me off of him and grabs himself! I’m like, “UM, Andy? Are you okay?” He responds, “BE QUIET!” After a minute of silence and while still holding himself, he says, “I was like, really close to, you know, blowing it? But I tried to stop it and make it go back in? I don’t know if it worked.” I climb back on the bed and sit next to him. We are both intently staring at it. He lets go and nothing happens for a second, then all of a sudden, it DRIPS out. Like seriously, it was throwing up or something. Very slow and one large drop. I’m sorry, that’s probably more than you needed to know… but seriously?! Who does that?!
Second time we do it (yes, I went back for more. He was so weird but hilarious… thinking back on it I shiver) he finishes just as quickly but doesn’t hold it in. He then gets up, grabs himself again, and runs out of the room screaming “IT’S MY DIABETES! I SWEAR!” I’d like to also add here that he does NOT have diabetes. He then developed a hernia and every day after class (we lived close to each other, so there was no avoiding the walk home from class) for the rest of the quarter we had to walk extra slow because his hernia was bulging and making him uncomfortable. Thank God for my sense of humor, or I may have died of humiliation for him!

Katie H:

My best friend, Talia, since 1st grade, was back home visiting from college. I was dating this guy Keith for about 3 months. [Or at least I thought I was, according to him we were just friends.] At any rate, 3 months of me even TALKING to the same guy is a big deal for me. So I was like hey Talia, want to meet the guy I’m dating? It was kind of a big deal for me. So we’re driving to his apartment and I’m thinking oh god, bad idea, he’s going to think she’s hotter than me and try to hook up with her. I voiced that thought to her, and she responded with “omg katie! i would never do that to you! we’ve been best friends forever, you’ve got nothing to worry about.”

I’m sure you can figure out what eventually happens based on that alone, but the incedibly awkward part was that it happened TWO HOURS LATER.

We get to Keith’s, and we’re all sitting on his bed playing video games, there’s not really a couch or anything bc it’s a studio apartment. My phone rings, and it’s my other bff Brian, so I go into the kitchen to take the call. The call lasts about…oh…I’d say, 5-10minutes tops.

Walk around the corner back to the bed and HOLY FUCK THEY ARE FUCKING.

There were Keith and Talia just fucking their little hearts out.

I had no idea what to do so I just turned around and walked into the bathroom, called Brian back and asked what I should do. For some reason my first thought was oh fuck I was Talia’s ride here, I can’t just leave her! But of course I could, and should’ve.

The worst part about it all was that my purse was at the foot of the bed. I unlocked myself from the bathroom, walked back over by the bed, put my hand up over my eyes and awkwardly said “Uhhhh don’t mind me!” in a sing songy voice as I picked up my purse and made my exit.

I was headed to Brian’s when I realized I left my favorite pair of super chic sunglasses at Keith’s apt, so I had to call Talia and ask her to just put them on the doorstep so I could turn around and pick them up without interfering in their fuckfest.

Wow. That was definitely the most uncomfortable moment of my life. Sounds like something straight off of Jerry Springer, but it was just so WEIRD that I couldn’t even loose my temper and get pissed off, I just wanted to get my shit and go.

Needless to say I don’t really associate with either of them anymore. Logically so.

Rob V:

My most awkward situation took place three years ago at my 1st grade son’s Christmas Program. During an intermission of the singing and skits put on by grades k-6, and with a completely full gymnasium, Santa showed up with a bag of gifts (in this case prizes). All kids were asked ahead of time to write a short essay of what Christmas meant to them and submit it. Santa chose a winner from each grade and they got to come to the center of the gym and sit by Santa and get a prize. My son won for the 1st grade class. Santa asked each child the usual sorts of questions and got the usual sorts of answers…until he got to mine. Santa asked if he had been good, and the answer of course was “yes!”. Santa asked if he helped out with chores around the house, and the answer was “yes”. So santa asked what he did to help his Dad at home with chores. My son replied, “My Dad has me walk to the mailbox to get the mail but he tells me to never open his
girl magazines because thats not stuff I am supposed to see”. I nearly shit. I get Maxim magazine and told him those were for me and not to open them up when they come, just because I didn’t think they were age appropriate. So now he is talking into a microphone in front of 1000 or so parents and spits that out. You could hear a pin drop in that gym!! I wanted to stand up and yell…it’s friggin MAXIM…not PENTHOUSE!!! My ex-wife was less than impressed as you can imagine. I still hear about that day a lot from people who were in attendance. I will forever be Pervert Rob who makes his poor kid run to the mail to snag his porn for him.