Disclaimer: I do not own The Vampire Diaries nor its characters. They belong to L.J. Smith, Kevin Williamson, Julie Plec, The CW Network, and whoever else.

Note/Warning: Because I miss Zach, and he deserves some fandom love.

We Would Only End In Tragedy

Jenna Sommers was always falling for all the wrong guys - and Mason Lockwood and Zach Salvatore could only watch and shake their heads and tell her the truth she didn't want to hear when she came to them for drinks and commiserating.

First was Logan Fell. Everyone knew he was an arrogant, self-centered, narcissistic bastard just like his father - his sisters weren't much different. Everyone, except Jenna. Oh, sure, he was as handsome as she thought he was, he was as smart and clever as she defended him to be - but he was a little too aware of it himself.

Not even Mason was as narcissistic as Logan - and Lockwoods were known for being self-centered dicks (if not specifically narcissists).

But Jenna couldn't see past the good looks and the smarmy charm and the easy, bleached-white smile and the attention to details - like, where a girl was most sensitive and what her favorite book was. She thought he was genuinely interested - not just keeping her happy so he could keep milking.

Still, Logan was understandable. He was a charismatic asshole who knew how to please a girl.

John Gilbert, on the other hand...Zach and Mason blamed it on Grayson Gilbert, and Miranda's hesitation to badmouth her brother-in-law for reputation's sake. Because even Jenna knew John Gilbert was a skeevy prick hung up on some girl that had ditched long ago.

Maybe it was the couple of years he had over her, the whole almost done with college, mature, older guy who wasn't all about drinking and hazing thing. Jenna went in and out of phases where she wanted someone like that. Maybe it was the fact that she was vulnerable, emotionally torn down by Logan's latest fling with a hot bimbo - and then John showed up in a car cooler than his brother's sports car and a leather jacket with an intelletual attitude. Jenna was helpless, no defenses.

Zach and Mason tried to warn her, but Miranda and Grayson encouraged.

It wasn't long before she was hanging with them at the Grill for drinks and commiserating again. Bemoaning her luck at always falling for guys with commitment issues. Though - to be fair, she said - at least John wasn't actively cheating, simply emotionally unavailable.

After a few more drinks, Jenna was arguing with herself over which was worse.

Mason said the bimbo flings.

Zach said the emotionally unavailability.

Both Logan and John knew what they were going to do to her, and what they couldn't offer her. At least Logan generally tried to stay away from hot blondes and leggy knock-outs. He was just weak-willed. John wanted a fill-in girl, and Jenna was easy prey.

Jenna Sommers was always falling for the wrong guys.

And Zach Salvatore could only watch, wishing he was some nameless schmuck that could ask her out without worrying when his 'distant' relatives might visit again.