17 months, 3 weeks, and 4 days. That's how long I've been crushing on Del, the cute IT guy down the hall. We've bonded over 80s music and Seinfeld references our younger-than-GenX coworkers don't quite appreciate. I'm pretty sure if I asked him out, there's a good chance he'd say yes. Just one problem. I don't take chances. I'm naturally risk-averse.

Okay, fine, let's call it like it is. I'm boring.

When our company hands out the worst employee appreciation gifts ever – leatherbound bucket list journals – I'm faced with just how deep my boringness runs. Trust me, it's deep.

It's so deep that after a week, the only item on my bucket list is to buy a scratch-off ticket. When this leads to Del and I sharing a modest lottery jackpot, I'm inspired to make a list for real, and inch my way outside of my comfort zone.

But is Del willing to wait around while I figure out how to live a little, or are inside jokes and an office crush all we'll ever have?