The Bet (Winslow Brothers 1)

“Okay, so maybe you got too close before? Someone special in a past relationship that you really felt was the one, but it didn’t work out?”

I shake my head again. Frankly, I’ve never really dated anyone I considered marriage material.

“Okay. So, what is it that brings out the need in you? Societal demands?”

“No, I don’t think so. I mean, I’m proud of what I’ve built in my business, and I realize I might not have gotten to do it this way if I’d met someone sooner.”

I can hear myself, and I imagine Dr. Winters must be getting frustrated with me at this point. Hell, even I am. But for as enraged as she may be on the inside, she doesn’t show any impatience on the outside. Since I’m genuinely confused at my own complication, it’s greatly appreciated.

“So, what’s the missing link here? What drives you?”

I shrug, fiddling with my fingers as I try to deep-think, and admit, “I’ve always pictured myself as married. As a little girl, I dreamed of weddings. I thought I’d have my own by now. It was in my ten-year vision, but…that was fifteen years ago. Honestly, I know what I’m looking for in a man, and I eliminate the noncontenders right off the bat. It should be saving me time.”

“Sophie, life doesn’t manifest like an Erin Condren planner. It’s messy. Unexpected. Usually drama-filled and ass-backward. You’re going to have to open yourself up to going on some dates with men who might not be Prince Charming.”

“I don’t see the point in dating people I know aren’t prospects for a long-term commitment. What’s wrong with that?”

“It’s judgmental. And shortsighted,” she says, her tone of voice somehow gentle enough to keep me from feeling bad. “Would you buy a house based on what it said on the listing, or would you actually do a walk-through beforehand to see what it was really like?”

My eyebrows pinch together. “So, men are houses now?”

“Sort of.” She grins. “You’re looking to set up shop…stay there for a while with both, right? Maybe the vinyl siding is faded, but the inside’s got a hundred-thousand-dollar reno, girlfriend.”

“You should start an app.” I grin cheekily. “HGTV meets that dating app TapNext.”

“I’m just saying that you can’t know the heart of a person until you spend at least five minutes in their presence.”

“What do you suggest I do, then? Because I’m trying, Dr. Winters, really. I’m willing to meet men. I’m willing to get out there. I want it.”

She considers me closely before leaning toward me again and tilting her head to the side. “Is that really true, Sophie? Are you really putting yourself out there? Because you just said before that you eliminate men who aren’t contenders right off the bat?” I frown as she continues. “What if you’re eliminating them too soon?”

The corners of my mouth turn down even farther, and she nods, decided.

“I’m giving you a homework assignment. Pick someone on the dating app of your choice, match with them, and go on the date. I don’t care if you already feel like it’s going to fail. I don’t even care if you give it a real mental chance. Just go. Get dressed up, make the effort, meet the guy, try to engage in enjoyable conversation, wait for the date to be over, and then say goodnight. No strings. No expectations, no anything. Just a date. Period.”

“You don’t think that’s a waste of time?”

“No. For you, I don’t. Dating needs to become a habit. Something you’re as comfortable doing as breathing. Once you relax and just take it all as a matter of course, one day, it really won’t be a waste of time. Because one day, you’ll meet the guy you’ve been looking for. And I can promise you this, he won’t be the one because he checks all the boxes on your list. You’re just going to feel it. And until you do, you need to go through the motions.”

Just go through the motions. Could I do that?

“You can and you will,” Dr. Winters replies as though she’s read my mind. “And then I’ll be here next week, ready to listen to everything that happened.”

One date. One night. One random chance. I could do that for a shot at happiness.

I mean…how hard could it be?

Monday, March 5th

Jude

“Where are you headed now?” I ask my brother, sliding my hands into my nice leather gloves and zipping my jacket up to my chin. It’s still frigid outside, even after the turn of the month to March, and the tunnel effect of New York’s busy streets only amplifies it. Combine that with being fresh out of the gym shower with still-damp hair and my nuts are liable to freeze to my thighs on my ten-block walk.

Flynn smiles—just smiles. God, he is such a mysterious bastard. Seriously. I spend a lot of time with him, mostly working out in the early evenings—it’s actually the reason I go to a gym in Midtown instead of by my place in SoHo—and yet, I don’t know that I actually have any knowledge to show for it. I don’t know what he does with his spare time, what kind of hobbies he enjoys—I barely even know where he lives, to be honest. I don’t expect I’d do very well in a trivia speed round about his life. He’s always been there whenever any of us has needed him, though, and that’s a hell of a lot more important than knowing what kinds of books he’s reading or if he’s into white-water rafting.