But by December 2010, both of their relationships had dissolved. As Hundertmark prepared to scale the wall at Sport Rock, Pepper walked over to say hi, mentioning that she hadn’t seen him in a while.
Hundertmark, a 38-year-old engineer, started talking about his recent travels, and the conversation quickly morphed into more personal topics, including the details of their breakups. When Hundertmark finally looked at a clock, he realized they’d been talking for four hours.
“All of a sudden we have this very deeply emotional, psychological conversation — much more than casual friends would normally have. We started to learn things about each other, including dirty, ugly gut-wrenching type stuff,” he says. “It was like free psychotherapy in both directions.”
Hundertmark was immediately interested in seeing Pepper outside of the gym, but she was wary.
“My thought was, just because two people had been through crappy breakups at the same time, shared suffering is not a reason to date,” recalls Pepper, a 34-year-old lawyer with a trade association.
For the next few months, they continued to bump into each other at the gym and sometimes even arranged to meet there; each time, the climbing gave way to lengthy conversations.
In May, while he was traveling for business in Asia, Hundertmark e-mailed Pepper and asked her out to dinner. “I think we get along very well, and we have a lot of things that are compatible,” he wrote, trying to make it clear that this would be a date.
Pepper agreed, but when he showed up at her house, she’d just woken from a nap and told Hundertmark, who was in a dress shirt and jacket, that she wasn’t going to change from her shorts and T-shirt. Still, they had a wonderful dinner and talked as easily as ever. When the check came, Pepper insisted that they split it.
When they said good night, Hundertmark left thinking, “That was fun. I have no idea if that was an actual date or not.”
For the next month they went on a series of what Hundertmark came to think of as “maybe dates,” because he could never get a read on whether Pepper was interested in him romantically. But they repeatedly stayed up talking until dawn, about topics that ranged from the substantive to the silly.
And though Pepper wasn’t revealing her hand, she was falling in love with Hundertmark.
When her birthday rolled around in late June, Hundertmark asked a mutual friend whether anything was planned for Pepper’s birthday. There was nothing in the works, so he arranged a dinner followed by karaoke. At the end of the night, as dawn approached, Hundertmark finally kissed her.
“I was very excited about this relationship, and I didn’t want to do something wrong,” he says. “So I was erring on the side of conservatism. Then by the time we did get physical, she was like, ‘Took you long enough!’ ”
Pepper had planned a solo skiing trip to Chile later that summer, but when Hundertmark asked whether he could join her, she happily agreed. As they lay on a hotel bed, he told her he loved her. “Okay,” she replied. “I love you, too.”
By the following spring, they were talking openly about marriage. Pepper knew it was right because she found herself being flexible in ways she never had before. “It was probably the first time in my whole life where I’ve been willing to compromise,” she says. “In the past I’d say, ‘Well that’s just me, that’s my personality, and if you try to change it, it wouldn’t be me.’ That’s an interesting stance, but it’s a good way to be alone for the rest of your life.”
In August, during a trip to Alaska that included hiking, mountain climbing and kayaking, Hundertmark proposed on a glacier below Denali Mountain.
On Dec. 1, the two exchanged vows in front of a fireplace at Dupont Circle’s Tabard Inn before 50 close friends and relatives. Pepper wore a white dress ordered from J. Crew, and the couple chose to have their ceremony officiated by a mutual rock-climbing friend.
“The good thing about getting married when you’re older,” Pepper reflected before the wedding, “is that you know absolutely what you like and what you don’t like, and more importantly what you can live with and what you can’t live with.”
Time shifted Hundertmark’s perspective, too, on what he wanted in life.
“I’m old enough to know there aren’t any perfect situations,” he says. “So when you find something that is much, much more good than any of the things that are difficult, then you grab onto it with both hands and you take the ride.”