'Awkward' Encounters: These Are The Most Unexpected Palos Hills Hookups

Tamara's tryst with Kyle was just one in a long line of flings-we-didn’t-see-coming

Love is blind, and the township of Palos Hills serves as some truly unarguable proof.


On Tuesday night’s Awkward episode, Tamara, who typically only has eyes for guys in high places, found herself strangely attracted to her high school class’ resident weirdo. Kyle, a formerly wordless lurker, apparently underwent some serious socializing during his freshman year of college, and almost immediately upon bumping into him at the Fourth of July party, Tamara found herself completely smitten. While she wouldn’t have touched Kyle with a 10-foot pole a year earlier, he suddenly seemed irresistible, and within minutes of re-meeting, the unlikely couple christened a bit of green space near the golf course’s 16th hole.

While shocking, the hookup -- upon closer inspection -- wasn’t so unprecedented. In fact, with the Awkward gang considered, the unexpected has proven to be pretty commonplace over the years. Look back at seven of Palos Hills’ wildest and most unexpected hookups below, and see what’s in store for the gang on the next new episode Tuesday night at 10/9c!

Sadie and Matty


A resolution was the furthest thing from Sadie’s mind on New Year's Eve during Awkward Season 2 -- instead, she used First Night to confess her feelings to longtime pal Matty McKibben. Even she was surprised when he answered her honesty by leaning in for a kiss, and though he eventually passed out during the encounter, the moment still left viewers awestruck.

Lissa’s Dad and the stripper


Palos Hills’ perfect Christian family was embroiled in a scandal when Lissa caught her bible-toting dad kissing a stripper during a house party. Eventually, the family learned to accept the gay patriarch, but his first step toward an honest life was certainly a shaky one.

Tamara and college student


Tamara wasted no time partaking in college’s customary “experimental phase.” During a visit to Southern Coast University (and after enough cocktails to qualify for Betty Ford), she found herself in the intimate company of a lady friend, Shane. Eventually, Tamara decided against pursuing something more meaningful than a one-night stand, but she’d always have the memory of her dorm-room romp…

Jenna and Ricky Schwartz

Would Jenna ever intentionally tongue her BFF’s crush? Of course not, but when Aunt Ally entered the picture in Season 1 and fed “Lil’ Bitch” some lil’ pills, all bets were off. Jenna’s makeout with Ricky amounted to her first big fight with T, and considering how sloppily the hookup played out, we can certainly see why.

Clark and Ricky Schwartz

Unfortunately, the late Ricky Schwartz didn’t leave such a favorable legacy. At Matty’s summer kickoff party, Sadie found her date Ricky swapping spit with Clark in rather unsavory fashion. Ricky may be gone, but nobody can accuse him of not living life to the fullest before passing.

Jake and that aggressive Palos Hills mom


Natalie’s first error in judgment: Bringing a baby to a loud, wild party spilling over with teenagers. Natalie’s second error in judgment: pursuing Jake, a high school student. It wasn’t so surprising that Palos Hills' most aggressive cougar baited Jake -- it was, however, surprising that he willingly latched onto the hook.

Val and The Bear

Sure, Val and Biggie eventually worked things out, but long before she saw her boyfriend’s true potential, she was just a woman attracted to mystery man dressed in a bear suit. During the Palos Hills senior class' ski trip, Val found herself mysteriously attracted to the lodge’s grizzly mascot, proving that just when you thought she couldn’t get stranger, she’d gladly prove you wrong.

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