The Rom Con

I think back to that trip and how bright-eyed and optimistic we were, reunited for the first time since we graduated and moved into new apartments, new jobs, and new relationships. How we stayed up late swapping stories of horrible bosses and money stressors and dating woes. How it had felt like there weren’t enough hours in each day to finish all the conversations we started. How we swore we’d make the trip an annual thing, committed to prioritizing our friendships no matter what.

“Anyway, that was the first and last girls’ trip we took before weddings and babies took over. I’ve been carrying around this stupid banana for six years and I can’t decide if it’s more depressing at this point to leave it on or take it off.” I toss the keys on the coffee table and sink back down into his luxurious couch cushions. “I really don’t want to be someone who begrudges other people their happiness, but sometimes I just feel . . . I don’t know, stuck in between. Or left behind. Do you ever feel that way?”

I finally pause for breath, and when I glance over at him, he’s quiet, his face expressionless. I can’t really read him. I’d like to think he’s just being thoughtful, but he’s probably trying to figure out how to politely remove me from his apartment. I seem to have careened right past “awkwardly personal” and straight into TMI territory.

I immediately regret my honesty. Why on earth am I telling him all this? I sound like some desperate husband hunter; a wannabe bridezilla on steroids. This is a rant best left to my single friends who can commiserate, or people who have no choice but to listen to me complain, like my mom. It’s Dating 101: Never whine about being single. Betty wags her finger in disapproval—Girls who whine stay on the vine!

I let out a self-conscious laugh and attempt to course-correct. “Sorry, got a little carried away there. Was that the kind of oversharing you were looking for? Rant over, I promise.” I seize my glass and shotgun the rest of my wine.

He holds up a hand. “Don’t apologize. Obviously, I can relate.”

I almost laugh out loud. I just bet Jack Bradford sits home alone, lamenting his singledom and crying into his beer. “Somehow I doubt that.”

He looks affronted. “Whose friends do you think all your friends are marrying?”

This time I do laugh, though my face still stings with embarrassment. I look around the room for a weapon I could use to put myself out of my misery. The aged-concrete lamp on the credenza looks heavy enough to do some damage.

There’s a ghost of a smile on his lips. “But seriously, you think men never have these kinds of thoughts? The things we worry about might look a little different, but I can assure you, we have insecurities too.”

“Oh yeah? Let’s hear ’em.”

He tilts his head, considering. “Just trying to figure out what women want is a huge source of stress. How do we show we’re interested without coming on too strong? What if we say the wrong thing? What if we misinterpret intent? Does she want someone better-looking, more athletic, smarter, funnier? Can we afford the life she wants? What if you don’t end up as successful as you’d hoped?”

“Well, you obviously don’t have to worry about that.”

“No, I get to worry about the opposite. Is she only interested in me for my money? Or because of this job and who I know?” He pauses. “Or in this case, will my job be a deal-breaker?”

Oh boy. He’s giving voice to the question I’ve asked myself countless times since this whole charade began—and despite my soul-searching, I’m no closer to an answer. I decide to give that last part a football field–sized berth and focus on the first part of his statement (and mess with him while I’m at it).

“Hmm.” I pretend to think about it. “For me it was mostly about your looks, but now that I know you know famous people, why don’t you hit me with a list of names and I’ll let you know how interested I am?”

He shakes his head sadly. “Terrible. You’re terrible. Making fun of a guy who just admitted to being insecure.”

“Oh please, you’re the least insecure man I’ve ever met. You’re about as insecure as the Dos Equis guy.”

He casts me a sidelong glance. “You’d be surprised.” It’s the second time he’s said that tonight.

“Prove it.”

He eyes me for a minute, as if weighing the wisdom of whatever he’s considering revealing, before nodding once. “Okay. Are you seeing someone else?”

It’s a good thing I finished that wine, because if I’d had any in my mouth, it would now be soaking the front of his T-shirt (which, come to think of it, would be a highly appealing visual indeed). “I’m sorry, what?”

“And look, I realize you don’t owe me an answer. You’d be well within your rights to tell me it’s none of my business. But I’d just like to know what I’m up against.”

Am I seeing someone else?! If he only knew how preposterous that idea is! I can barely keep my current multiple personalities straight without adding another human being to the mix. Honestly, I’d think he was kidding if he didn’t look so serious. Jack Bradford—he of the model-perfect bone structure, certified alpha male, a literal leader among men—is insecure about me?

“What you’re . . . Am I . . . Jack, you’re . . .” I can’t form sentences. I’m stuttering through the alphabet. I stop and start again. “May I ask where this is coming from?”

He exhales a breath. “You’re very hard to read. You wait days to text me back. In fact, I’d just about decided you were ghosting me when you called and offered to cook me dinner. I couldn’t figure out if I should be taking the hint or trying harder.” He’s ticking them off on his fingers. “I tried to pin you down all week but you said you needed a rain check, then very specifically didn’t say what you were doing. Not that I’m entitled to an explanation of your whereabouts, but it makes a guy wonder. Wouldn’t be the first time I assumed the wrong thing and paid for it later.” Whatever he’s referring to seems to disturb him, and he shakes his head. “I guess I thought we were on the same page after Times Square, but this past week I felt like I was back to chasing my tail. It’s messing with my head.” He swallows and I watch a muscle tic in his jaw, tight as a drum. I’m tempted to trace it with my index finger. “This is going to sound obnoxious and I don’t mean it to be, but I’m not used to having to guess if a woman is into me.”

Whoa. I blink a few times, caught off guard as much by his honesty as by my own tangle of emotions. My heart’s doing something funny in my chest, leaping and fluttering against my ribs like a butterfly on a sugar high. Jack is jealous! He doesn’t want you seeing anyone else! He’s a knight mounting his steed, ready to vanquish the enemy for your heart!

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