Page 83 of Up All Night

Hypothetically, if we ever dated, would it work? This conversation felt like research. I couldn’t help comparing myself to the guys she had dated, and I had to admit I stacked up favorably against all of them—like how I would never cheat on a woman, I would never again let someone’s schooling or career choice keep me from dating them, and I rarely drank and never partied.

I reached for my fork. “I do want to hear about it. Friends learn about each others lives and how they ended up where they are today.”

I hoped my answer wasn’t too honest. I didn’t want to scare her away, but I did want her to know I was genuinely interested in her life. Hopefully throwing in the word ‘friends’ would make my answer seem less intense.

“Okay,” she smiled. “But you’re up next.”

Crap. I hadn’t thought things through. Although I hadn’t had as many relationships as Halle had. She already knew about my high school girlfriend, and I’d already told her some of what had happened with Rachel, the only other serious relationship I’d had.

I looked at my watch. “If we have time,” I teased.

“Oh, stop it. I haven’t datedthatmuch. I’m almost done.”

“Uh-huh, sure.”

She ignored me and continued with her story. “Troy broke things off after we’d been dating for a while because we weren’t progressing in our relationship. He said he wasn’t unhappy with me but that the thought of furthering our relationship by either moving in together or getting engaged made him physically ill. He felt like he shouldn’t keep dating someone he couldn’t see himself having a future with.” She took a bite of her food like the rude words of her ex were no big deal.

“And how did you feel about that?” She must have been crushed hearing her boyfriend tell her that thinking of them still together months down the road made him sick.

She shrugged, chewing her food. “Honestly, I was fine with it. Once he said his thoughts out loud, I realized we were more like friends than a couple. I didn’t want to further our relationship either. It was a quick and painless breakup.”

I studied her to see if she was masking a deeper emotional reaction. Each guy, each breakup she’d talked about seemed to mean nothing to her. Had she ever dated anyone she truly liked? Or was she hiding any emotions she might be feeling from me because she worried it might ruin our evening? It bothered me that I didn’t know her well enough to tell how she was actually feeling about all this. Which was dumb, since we hadn’t known each other for very long. Still, I couldn’t help wanting to be someone she could confide in.

“That’s good, I guess,” I said, not quite knowing how to respond.

She pushed her food around her plate. “Then my last boyfriend was Jeremy.” She paused but continued to move her food from side to side. I wasn’t a mind reader, but I could see the wheels turning in her head as she worked to find the right words. She tucked her hair behind her ear and kept her eyes on her plate. “We dated for almost two years, and things just fizzled out.” One shoulder lifted in a shrug before she quickly shoved a large bite of food into her mouth.

Okay, so that was clearly a sensitive subject, and she obviously didn’t want to unpack it today. Which had me wanting to know about this Jeremy guy even more. Why had things fizzled out? The way she’d said it made it sound like there was a lot more to it than their relationship going stale. And how long ago had they broken up? Was she still nursing a broken heart?

I kept the questions to myself. This wasn’t the time or place to push a topic she didn’t feel comfortable talking about. Was it dumb of me to hope that one day she would feel safe talking to me about him? Although talking about a guy who had clearly broken her heart wasn’t at the top of my list of fun things to do.

“Your turn,” she said, her mouth still full from the big bite she’d taken.

I finished chewing my food, wondering how much detail I should give her. There had only been two girls I had wanted to have a long-term relationship with.

I wiped my mouth with my napkin. “There isn’t much to tell. You already know about what happened with my high school girlfriend.” I placed my napkin back on my lap. “And then the only other girlfriend I had was Rachel, and I’ve already told you a little bit about our breakup too.”

“You’ve only had two girlfriends?” she asked, sounding surprised.

“Yeah,” I answered. “In college I focused on school, and then since college I’ve been focused on work. I’ve dated, of course, but I’ve never been tempted to get into a committed relationship.”

“Except with Rachel,” she pointed out.

I let out a breath of air. “Right, except with Rachel.” I hadn’t realized how uncomfortable it would be to talk about my exes, which had me feeling bad I’d made Halle tell me all about hers. I didn’t even have any feelings for Rachel anymore, and I still didn’t want to talk about her with Halle.

I grabbed my drink and took a sip.

Halle patiently waited for me to tell her more details about my relationship with Rachel. Since we were just friends, it shouldn’t feel weird to talk to her about this, but now that the tables were reversed, I couldn’t help but feel awkward. Probably because my feelings for Halle were far more than friendly. Today hadn’t been supposed to feel like a date, but sitting here under the stars, with twinkling lights strung above us—well, there was no getting around the fact that it looked and felt like a date.

I fidgeted in my seat, trying to figure out how to talk to her about my ex-girlfriend. “Uh…” I cleared my throat. “Rachel and I actually met in college, but we were more acquaintances than friends back then.” I straightened the butter knife next to my plate. “A few years later, we ran into each other, and I ended up asking her out. Things progressed naturally, and soon we were a couple. Like I told you before, we both worked crazy hours. You know how I am at my father’s company, and Rachel is a chemical engineer and also spent a lot of time at work. When we were home together, we both kept working. Neither one of us could seem to leave work at work.”

“Sounds romantic,” she cut in, a playful smile on her lips.

I chuckled. “Yeah, we were both workaholics.” I slowly spun my glass, giving my hand something to do. “She was better about not working on the weekends and planning out time for us to spend together, but I struggled to put work out of my mind. Eventually, our weekend couple time turned into just Sundays, which turned into every other Sunday until we were hardly seeing each other at all. She wanted more from me, and I wasn’t at a point where that was something I could do. With as rarely as we were seeing each other, our relationship wasn’t really a relationship, and she didn’t want to be with someone who wasn’t willing to make time for her or even try to have a better work life balance. I completely agreed with her and apologized for not being able to be that someone for her. She deserved a better man than me, so we ended things.”

She chewed a bite of food, looking thoughtful. “I’m trying to think of what to say, but all I can think of is how sad that story is.”

I scooped more food onto my fork. “If it makes you feel any better, I think it was a good thing. It was for the best.”

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