After Paying a Year’s Debt, I Dated His Boss

I stood outside the restaurant's private room, a custom pen clutched in my hand. For a full minute, I couldn't bring myself to push the door open. It had been left slightly ajar, and Derek Shaw's laughter came out. "Claire bought you a watch, covered all your bar tabs, and even bailed you out of that investment mess last year," someone said. "You really don't plan on dating her for real?" Derek let out a disgusted snort. "Date her? Then who's going to foot all my bills?" The room erupted in laughter. Little by little, the hand gripping the gift box went ice-cold. "Every time you turn her down, you introduce her to some other guy," another person laughed. "This time you gave her Graham's number? Aren't you worried she'll actually run off with your friend?" "She didn't contact any of the other guys," Derek replied lazily. "She thinks I'm testing how much she loves me. The more she turns those guys down, the more convinced she is that she's passed my test." He gave a chuckle. "As for Graham? I never even mentioned her to him. Even if she contacts him this time, he won't pay her any attention. She'll come crawling back to me eventually." "You sound pretty sure." "Of course I am. I've drilled it into her head that she doesn't believe she can meet anyone better than me. She can't even function at work without me, and she's just as dependent on me emotionally." He paused, and that familiar, smug certainty seeped into his next words. "Claire isn't a woman to me. She's just my free credit card." I stared down at the pen in my hand. The clip was engraved with the date of Derek's first industry award. I'd waited 6 whole weeks for the custom piece, planning to give it to him tonight as a thank-you for mentoring me all these years. Now, the only person I owed thanks to was myself. At least I hadn't opened that door. Derek always told me my ideas would embarrass the company. Then he'd turn around, steal the best parts of my work, pass them off to clients as his, and hand me a coffee afterward while telling me he was the only person willing to put up with my "unprofessional attitude". That twisted dynamic had left me feeling helpless. Little by little, I'd become dependent on him until I started believing I couldn't survive without him. I'd mistaken his control for caring and the occasional scraps of tenderness he threw my way for genuine affection. For an entire year, every time I confessed my feelings, he'd turn me down, then casually suggest some other guy I should date instead. First, it was a college buddy. Then, it was a single client. But he always watched my reaction. The moment I turned someone down, he'd become a little nicer to me. And I thought it was all some kind of test. I thought that if I kept choosing him, he'd eventually admit that he cared about me too. That's why I hadn't contacted any of those guys the first few times. Then, the last time, he gave me the number of a guy named Graham. "You two would probably be a better match," he'd said. That day, I didn't turn him down immediately like I always had. I was exhausted. I was desperate to escape that endless test. So, for the first time, I answered, "Okay." That had been 3 months ago. I'd saved Graham's number out of spite and sent him a quick introduction. He'd replied with nothing but a single question mark, and I'd been too embarrassed to reach out again. Then, a month ago, we started talking again. Yesterday, he'd called and asked if I wanted to make things official and become his girlfriend. I said yes. But Derek had just admitted that he'd never even mentioned me to his friend. I didn't care about the stupid pen anymore. I didn't even care about all the money I'd wasted on Derek over the past year. What made my stomach churn was knowing that I'd handed him my whole heart, only for him to weigh it for a moment before turning to his friends and gloating, "Look, she fell for it again." I threw the gift box into the trash can and headed straight for the elevator. My phone buzzed. Derek was calling. "Where the hell are you?" he snapped, impatience dripping from every word. "We need to pay the bill here. I left the company card back at the office. Cover it for now. We'll sort it out tomorrow." Before today, I would've rushed inside without hesitation. But this time, I glanced at my reflection, my face pale but calm. I let out a laugh. "No." The line went dead silent for 2 full seconds. "What did you just say?" "I said it's your birthday. You can pay your own tab." "Claire, cut the crap. You've been dying to prove your sincerity, haven't you?" So that was what it had always been. He'd never even had the decency to call what I felt for him "love" or even "liking". To him, it was always just "sincerity." Like I'd been trapped in some endless job interview, with him as the only person holding the scorecard. "Not anymore," I said flatly. "I'm done chasing you. And I'm never paying a single cent for you again." He snorted, like he was listening to a toddler throwing a tantrum. "How long do you think that's going to last?" "That's none of your business." I pressed the elevator button. "For your information, I'm already dating Graham, the last guy you set me up with." I hung up before he could say another word. The elevator doors slid slowly shut in front of me. My eyes burned, but I didn't look back.