awkward

UPDATE: Confess Your Crush with Nate and Sydney

Did the cutest Confess Your Crush ever turn into the cutest date ever? Let's find out!
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Jenn's The Worst Neighbor

Poor Jenn was stuck in a really awkward situation when she tried to give her neighbors a gift.
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Storytime With Jeff: Greg's Personality Test

Jeff learned there's consequences to asking your Father-in-Law for help...
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An Awkward Family Christmas

Kelly's friend is about to walk into a very awkward Christmas...What awkward family moments are you about to have to deal with?
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A Bad Boss Christmas

If you thought your boss was the WORST, would you still pitch in for an office gift for him?
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Explain This To A Five Year Old

It's Jenn's new game! When a child finds something for 'Adults Only' and asks what it is...what are you supposed to say?
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Proposal Denied

Some of these reasons for denying a proposal sound a lot more legit than others...
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Confess Your Crush: Adam and Rebecca

He likes his barista a whole latte, but he couldn't have been more awkward about it.
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Confess Your Crush: Bonnie and Perry

She's had eyes for her coworker since day one. Let's hope he feels the same!
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Do-Not-Answer Roulette

Jenn's calling a random number listed as "Do Not Contact" in either Jeff or Kelly's phone. Who's gonna pick up?
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