**Prelude** I casually brought up online dating with my boss, testing the waters. Meeting in person? Not an option. What she didn’t know? Her mystery boyfriend was one of her employees. **Prelude end** She DM’d me: “Hey, can I send the photo privately?” Me: “Uh… sure, I guess?” A second later, the photo came through, and I nearly choked on my coffee. “You’re 5’9”? More like 5’1” tops,” I muttered to myself, staring at the picture. It was a mirror selfie taken at the worst angle imaginable. Her head looked enormous, her body tiny, and those black-framed glasses? Pure IT-department chic. But under all that? She was gorgeous. Still, I couldn’t resist: “Okay, first things first, those glasses? Toss them. Get contacts or frameless ones. Next, stop taking photos from that angle. It’s an insult to your face. Tilt your phone higher, angle it down slightly. And lose the baggy clothes. They’re not doing you any favors. Try a shorter black skirt or something.” Her response was immediate: “Wow, thank you so much! I’ll try that!” I figured that was the end of it. Spoiler: It wasn’t. The next day, she sent me another photo. “Better?” I sighed. “Lose the floral pattern, try something solid. And you’re still angling the camera too low. Hold it higher, like I said.” “Got it!” Day three, another photo. “Am I improving yet?” I groaned. “Okay, now we’re getting somewhere, but change your shoes. Those flats aren’t helping. Go for heels. Something sleek, maybe nude or black.” By day five, I was about ready to fake my own death. Then she hit me with: “Hey, can I pay you for your advice? Like a consultation fee?” I raised an eyebrow at my screen. “Uh… sure?” When she added me on Snapchat, her profile picture almost gave me a heart attack. No way. It was her. My boss. She messaged me instantly: “Thanks again for all your help! Just a little something to say thanks.” Attached was a $5,000 transfer. I stared at the number like it might disappear. “Well, who am I to say no to generosity?” I mumbled, shamelessly hitting “Accept.” After that, I kept helping her. She was a fast learner, and before long, she went from clueless to stunning. Then, just as I was planning my quiet exit, she dropped a bomb: “Hey, there’s something I’ve been meaning to tell you…” I froze. “Uh, okay?” She sent me this long, dramatic love letter, like something out of a YA novel. I skimmed past the flowery prose to the last line: “I think I’m falling for you.” I stared at it for a good minute before typing: “Thanks… I really appreciate it!” She replied almost instantly: “Wait, what? No, I mean I like you!” “Wow, uh, that’s… really flattering!” “Flattering?!” “Yeah, I mean, it’s sweet. Thanks!” There was a pause, then: “So… does that mean you’ll give me a chance?” I stared at my screen like it might explode. “Uh… let me get back to you on that.” She took my vague deflection as encouragement because the next morning, she started texting me non-stop. “Morning!” “Heading to work!” “Just got to the office!” “About to grab coffee!” It was cute, if not slightly overwhelming. Then, a month later, I screwed up. Big time. I was scrolling through Instagram, saw a photo of a gorgeous model, and sent it to a buddy with the caption: “Bro, I’d simp for her any day. Absolute perfection.” Except… I didn’t send it to my buddy. I sent it to her. Her reply was immediate: “???”