Before their first date, Kenny Thompson told Jessica Wright that they were going to get married.
“I really believed it,” recalls Kenny, former director of messaging for Vice President Biden and current director of external affairs for PepsiCo in New York. “I never thought when you find the one, you just know. . . . It’s really weird. Something clicks and it’s like, yes, this is it.”
Jessica, past White House director of scheduling and now deputy chief of staff for New York Mayor Bill de Blasio, was not convinced. “What are you talking about?” she replied, laughing it off. She liked Kenny’s personality, humor and confidence, but marriage? Really?
Kenny, now 33, and Jessica, now 31, met in Des Moines during President Obama’s first presidential campaign. Back then, Jessica was the deputy director of scheduling and Kenny was part of Obama’s national advance team.
Prior to meeting face-to-face in December 2007, the two exchanged e-mails for months, planning Obama’s daily, minute-by-minute schedule and the advance team’s visits across the country.
“It was really strange because so often you e-mail with people, you hear their voices, but you don’t actually know them,” Kenny says. “It was really the epitome of ‘I know who this person is, but I don’t really know this person.’ ” Their initial meeting was brief, because of the craziness of the campaign and Kenny’s hectic travel schedule, but they were finally able to put a face to a name.
At the end of the campaign, both were offered positions at the White House and began to see each other more frequently.
“She was essentially planning all of my trips,” Kenny says. “I was on the road, and she was in the office.” They became work acquaintances and ran in the same circle of close-knit friends.
Kenny told Jessica his prediction the first time they saw each other socially outside of work at a colleague’s goodbye party in Dupont Circle. In spite of his bold remark, Jessica was not scared off and they continued to see each other often at happy hours and get-togethers.
In summer 2010, Kenny left the White House to accept a position at the U.S. Trade Representative office. Realizing how much he missed seeing Jessica regularly, he found himself frequently calling her work line just to check in and say hi.
Finally, in November 2010, he worked up the nerve to ask her out for drinks after work at BlackFinn American Saloon in the District. She said yes but wondered whether it was a date.
Her question was soon answered. After learning that some coworkers were meeting up elsewhere for drinks after work, she e-mailed Kenny and asked whether he wanted to join them instead. He replied with three words: “No, I don’t.”
At BlackFinn, the conversation came naturally. Toward the end of the night, Kenny leaned in for a kiss at the bar, but Jessica backed away. “She was like, no dude, back off,” Kenny remembers. It was too much too soon. Kenny tried to jokingly play it off, asking Jessica, “Why are you being weird?”
“I thought that maybe I had misinterpreted it,” Jessica recalls. “Maybe he wasn’t trying to kiss me and I did make things weird.” Despite the awkward moment, she was intrigued and wanted to get to know him better. Both realized there was something special there, and dinners, drinks and dates followed. Soon, a strong relationship developed. “It happened really seamlessly,” Jessica said.
Jessica loves Kenny’s wit, thoughtfulness and confidence. “He really owns a room,” she said. “He is one of those people that can have a conversation with anyone. He is the center of energy in any situation he’s in.” Kenny is drawn to Jessica’s intelligence, calm demeanor and sincerity.
Although their perspectives on many things are quite different, they do share common values, interests and goals. “Our biggest challenge was getting on the same page about what we wanted our relationship to be and how to best be together as a team versus two individuals who really love each other,” Jessica says. “The thing that makes us a true team is the fact that we both have such opposite strengths and weaknesses. Together, we are a whole person.”
Both are very independent and driven. “I had been living as a single woman for a long time and knew how to take care of myself. I didn’t really need anything,” Jessica says. “It took me a while to get to a place where I could let him help me and be there in the way that he wanted to be.”
But when she did, she realized just how much she cared for him. He came through for her early in the relationship during a stressful apartment move. He went with her to Ikea, carried all of her new furniture and helped her dispose of old stuff she didn’t want. He turned a typically terrible and taxing experience into a silly and enjoyable one.
For Kenny, it was a gut feeling. “I am an only child and I love being by myself, but even when I want to be by myself, I want her next to me,” he said. “Never in my life have I felt that way about anything or anyone.”
Jessica agrees. At one point, she realized, “I never wanted for him to not be around.” “He was just the dude I wanted with me forever,” she says.
They planned a long weekend in Santa Monica, Calif., one of the couple’s favorite vacation spots, for Jessica’s 30th birthday last April. He planned to propose to her at dinner after catching a Los Angeles Clippers basketball game. In an effort to hide the ring, he stashed it in a clump of scotch tape in his pants watch pocket.
Nervous, he kept a close watch on the ring throughout the entire game. “He definitely went to the bathroom at least five times. . . . I was like, what is he doing?” Jessica says. “It turns out it was because he was checking to see if the ring was still there.”
After the game, they decided to delay dinner and walk to Palisades Park in Santa Monica to watch the sunset. Ever the advance man, Kenny knew this was the perfect setting. He dropped to one knee and proposed.
Two days later, the president congratulated them on their engagement at a White House event. “A beautiful couple. We love them. They are wonderful,” President Obama gushed to the crowd. “They’ve been loyal, shown such great friendship to me, and I’m so glad that they have gone ahead and taken the plunge.” The pair moved to New York in February.
Kenny Thompson and Jessica Wright exchanged vows March 22 in a grove of linden trees in front of 130 guests at Washington’s Meridian International Center. After the wedding, they honeymooned for a week in Playa del Carmen, Mexico.
“We were work colleagues, then friends, and now we get to spend the rest of our lives together,” Kenny said before the wedding. “My prediction was correct.”
“And I get to marry a psychic!” Jessica chimed in, jokingly. She looked over at Kenny and smiled. “He knew all along.”