CHAPTER ONE
ON THE THIRD DAY of ninth grade, Jack Nolan asked Maggie Doonan to be his date to the Leo Catholic freshman dance. He blackmailed his older brother, Michael, into dressing up as a chauffeur and driving them in their father’s baby-shit-colored Lincoln Town Car. Then he sweet-talked Mrs. Jankowski at the flower shop into finding lilacs in Chicago, in September, just because Maggie’s sister had told him that they were Maggie’s favorite flower.
After that, Maggie Doonan hadn’t needed any more convincing that he was the perfect half-formed man for her. And the fact that he was an actual, honest-to-God choirboy had convinced Maggie’s father not to even bother threatening him with the shotgun that still resided in the Doonans’ front closet.
At the time, Jack had no idea what kind of power he had unlocked.
Two years later, he and Maggie had sullied the back seat of the baby-shit-colored Lincoln Town Car in unspeakable ways. And, two years of near constant shagging after that, he’d watched her get in her parents’ SUV to leave him for Harvard.
Watching Maggie’s tearstained face drive into the distance had broken Jack’s heart. But he’d been the only guy in his high school friend group to leave for college with valuable sexual experience not involving his right hand.
Still, he’d been sad.
Until he met Katie Leong during the third hour of freshman orientation at the University of Michigan. She’d winked at him while they’d learned the fight song at some stupid mixer for first-year students. That wink had hooked straight into Jack’s dick and driven him to be the best college boyfriend ever—midnight burritos, romantic two a.m. walks to and from the library, and oral sex at least three times a week—six times during finals. Hell, he’d even started working for the school paper because Katie was going to be a journalist when she grew up.
The only thing about his relationship with Katie that had stuck past her semester in Paris, and her subsequent new relationship with some French douche named Julian, was his career in journalism and a broken heart.
But the broken heart had lasted only a few months—until he’d met Lauren James, his favorite ex-girlfriend. She was off-the-wall funny and could suck the chrome off a trailer hitch.
He and Lauren had lasted through their senior year at Michigan and a shitty apartment with six roommates in the Bronx while he’d studied for his master’s at Columbia and she’d waited tables at a craptastic Midtown tourist trap and raced to and from off-off-Broadway auditions.
Lauren hadn’t even dumped him when he’d moved home to Chicago for a shiny new job. She’d saved her tips and flown out twice a month until she’d met a British director who wanted to cast her in an all-female West End production of Waiting for Godot.
You’re the best man I know, Jack. Such a great guy. I’ll never have another boyfriend like you.
No, she wouldn’t. Because she married the prick director after the very brief run of the show. That British guy hadn’t been a Boy Scout, and he for sure didn’t know all the best sex knots to tie.
As he stood at the bar of a speakeasy in Wicker Park, after waiting fifteen minutes for an artisanal old-fashioned made with, like, artisanal cherries and orange peels scraped off with the bartender’s artisanal hipster fingernails or some shit, he’d been without a girlfriend for six months. It was the longest he’d ever gone, and that was why his buddies had thought it was a good idea for him to leave his couch—and the Michigan–Notre Dame game—to sit around and talk to them in public.
He should be working tonight. In addition to not having a girlfriend, he didn’t have the illustrious journalism career he’d dreamed of. In a recent pivot to video, he’d become the online magazine’s how-to guy. His boss told him he was “too handsome to break real news,” but more important, he would be laid off if he didn’t shift with the times.
Now his father grumbled about him “not having a real job” every time he saw him, and Jack kept his mouth shut because he was living in a condo his family owned. If he lost his not-real job, not only would he have to hold his tongue around dear old Dad, he would have to wear a sandwich board on the corner. Or worse, work with his dad. While his father could deal with his working a job outside of the family construction business, he wouldn’t be underwriting Jack’s lifestyle if he got fired.
He loved his father—looked up to him—but they would kill each other if they had to work together.
So, he was here with his buddies, trolling for ideas for his next bullshit column. Chris and Joey could be his guinea pigs for whatever he came up with. He’d grown up with them; they’d all graduated from Leo together. Unlike him, they were knuckleheads about women. The idea that they would need to stage some sort of intervention with him over the nonexistent state of his love life was freaking preposterous. As demonstrated by the fact that they were wearing suits for a Saturday night out in the hipster hell that was Wicker Park, so they could stand around a bar that served overpriced, fussy drinks while looking at their phones and not talking to any of the women actually in the room.
Neither of them understood that for the first time since Maggie Doonan had put her hand down his pants under the bleachers at the freshman dance, he was kind of happy being alone. He could finally do the kind of shit that he liked—watch the game with a beer or five, sleep until noon, bring bread into the house without ruining someone’s gluten-free cleanse.
For the first time in his adult life, he was figuring out what he liked instead of contorting himself into the kind of guy Maggie, Katie, or Lauren needed. And he meant to go on that way.
Just the other day, he’d been thinking about getting a dog. Some slobbery beast—like a mastiff or a Saint Bernard. Lauren hated dogs. Which probably should have been his first clue that the relationship was doomed.
Still, he scanned the dark bar to see whatever other unfortunate souls found themselves ripped from the warm embrace of their college sports or Netflix queues. No one looked quite as miserable as him, though. Not a single one of the long-bearded hipsters littering the red leather couches and old-timey booths looked like he’d flash a nun for a beer on tap.
Looking around, he thought maybe his next video could be How to Not Ruin a Saturday Night Paying for $15 Drinks at a Douche-Magnet Bar. Name needed work.
His gaze stopped right next to Chris and Joey on the ass of a woman in a tiny black dress that didn’t match her gray moccasins. He didn’t give a shit about her sartorial choices because there was so much velvet-soft-looking light-brown skin between the shoes, which looked as though they’d seen better days, and the bottom of that dress, which made Jack’s lungs feel like they were going to combust. He hadn’t even seen her face yet, but he knew that she was like whisky in woman form; he felt his judgment cloud and high-minded ideas about bachelorhood vacate the premises. In his head, she was already like the first puff of a cigar. Just her gorgeous legs made his throat itch and burn. Forty or so inches of skin had him choking on lust.