Cringe-Worthy Laughs: Awkward Jokes to Make You Squirm.

Prince Harry’s bachelor party had to be pretty awkward.
He was putting pictures of his grandma in a strippers G string.

I went to a 4-year olds birthday party once, it was kinda awkward...
...probably because I wasn't invited...

It’s always awkward the first time you hold hands with someone... because they usually want to know who you are.

My life is just a series of awkward and humiliating moments separated by snacks.

That awkward moment when you're about to hug someone sexy as hell and then you hit the mirror.

That awkward moment when the woman you’re dancing behind bends over so you can grind it. But it turns out she just dropped an earring, and no one else in Mcdonalds can hear the music on your iPod.

My window cleaner caught me masturbating today. It was awkward.
Maybe I shouldn't have been standing in his garden.

My sister and my new girlfriend have the same name. That‘s so awkward... now every time we have sex I gotta think about my new girlfriend.

My wife reckons that recently I have become an awkward, arrogant cunt, and she just can't understand me.
Seems like my French classes are going really well.

If you think buying condoms is awkward,
Try returning them. I haven't been laid in forever.

My wedding night with my wife was awkward...
When we undressed I told her she was beautiful and looked like a goddess in the moonlight. She told me it looked like my hard on was trying to ask my butt a question.

My proctologist tried to ease the awkwardness after the unexpected orgasm by telling me it's perfectly natural.
I just wish he'd have aimed away from me.

A pirate awkwardly stumbles into a bar.
Bartender: What's wrong?

Pirate: Aye, a scallywag shoved me boat's steering wheel down me pants and it's stuck there in me crotch!

Bartender: That sounds painful.

Pirate: Aye, it's a driving me nuts.

A girl suggested I set up a double date to make our first time out less awkward.
I really hope my parents like her.

My nerdy friend got a Ph.D on the History of Palindromes.
He’s now Dr.Awkward.

That Awkward moment when you pay $2 for Evian water.
and notice if spelled backwards your Naive.

It's awkward touching hands with a woman in a popcorn bag.
Especially if you don't know her and she doesn't know that you're eating her popcorn.

That awkward moment when at the end she wanted a handshake, but you went on for a full french kiss
That job interview wasn’t really going anywhere, anyway.

What's the difference between awkward and uncomfortable?
Underwear can be uncomfortable, but when you involve other people in the problem it gets awkward.

I was watching porn last night when my grandmother suddenly walked in.
⁠ It was an awkward way to find out what she did for a living.

My first orgy was an experience to remember. I expected to it to be full of awkwardness and disappointment.
But thankfully all my cousins were really supportive.

That awkward moment when you're having sex with a German girl and she keeps yelling "Nine!"
Like, are you just yelling your age or are ten of us too many?

I went on a date for the first time and it went very poorly.
My wife agreed it was very awkward and told me we shouldn't try it again any time soon.

My girlfriend bought me the karma sutra.
Which put me in a very awkward position.

I wanna try asking out my school crush, but it might come off as awkward.
Man being a teacher is hard.

That awkward moment when you tell a chemistry joke, and get no reaction.
I guess all the good chemistry puns argon.

I hate shower sex.
It's slippery, awkward, and one of the worst things about prison.

Giving prostate exams is one of the more awkward parts of being a doctor.
I just hope my patients don't realize im a dentist.

What happens when you get a 100 socially awkward people together in a room?
Nothing.

The first time I had sex, it was in my parent’s bedroom. My girlfriend giggled nervously and moaned, “This is a bit awkward.” I grunted...
“Just ignore them!”