To Gillian Ramsey’s friends, it seemed as though the guys she dated were all the same: hung out in Georgetown, were always up for a good time but didn’t call when they said they would.
So in April 2010, when she heard about a local radio DJ from Mix 107.3 who was attempting to go on 30 dates in 30 days, Ramsey decided she would do the same.
“I was like, ‘I can totally do 30 dates in 30 days,’ ” recalls Ramsey, a 29-year-old former pageant contestant who was teaching kindergarten at Holy Trinity School in Georgetown at the time.
The parameters were set: prospective suitors had to be within 10 years of Ramsey’s age and live within a 30-mile radius of the District. Friends-of-friends and colleagues’ acquaintances were recruited to help to fill the slots. Outgoing and bubbly, Ramsey could chat easily with each of the men, but it wasn’t always fun.
“When you go on that many dates, you have the same conversation 30 times. ‘Where have you traveled? What’s your family like? What did you study in school?’ ” she recalls. “It was exhausting.”
Sometimes Ramsey would schedule two or three dates for a single night, just to give herself the next day off. By date 28, she was ready for it to be over. But date 30 was already scheduled; she just needed to find No. 29 for the challenge to be complete.
As she and a friend sipped margaritas at a bar in Arlington, they spotted a tall, kind-looking man who might fit the bill. Ramsey filled him in on her endeavor, and they chatted for 15 minutes before lining up a date for that weekend.
John Sheahan X, who has the same name as his father, grandfather and generations of ancestors, wasn’t used to being approached in bars. The Justice Department lawyer’s marriage had begun to unravel in 2008, and as a single father to a young son — John Sheahan XI, of course — he was just beginning to dip back into the dating pool.
Sheahan, a 39 year-old trivia buff, suggested that rather than meeting for coffee or drinks, they try the Post Hunt, an annual scavenger hunt sponsored by The Washington Post Magazine.
“Honestly, I considered her so far out of my league that I didn’t think I had much to be nervous about,” Sheahan recalls.
As they walked the city trying to unravel the game’s clues, they talked without pause — which doesn’t come often for Sheahan, an introvert. “I just didn’t feel any reserve. I didn’t feel any barriers,” he remembers.
They finished with a drink at the W Hotel and texted for the remainder of the night after saying goodbye. The next day, Ramsey canceled date 30.
She and Sheahan saw each other almost daily for the next month until Ramsey left to spend the summer at the New Jersey shore; she invited him to visit anytime.
The morning after she arrived, he called to ask whether he could come up that day. “I broke every single rule about trying to stay cool,” Sheahan says.
In July, he invited her to come to his class reunion, which was being held in California because one of his former classmates from St. Anselm’s Abbey School in Northwest Washington was undergoing cancer treatment in San Francisco.
Sheahan’s tight-knit friends from the small all-boys school heartily approved of Ramsey, which reinforced what Sheahan had already begun to think: He wanted to marry her. But they’d only been dating a few months, and he knew that getting engaged so soon would seem crazy to others.
That November, they traveled back to California, this time for his friend’s funeral. One loving eulogy after another talked about doing what felt right when it felt right and not wasting a second of life.
On the long flight home, Sheahan told Ramsey, “I’ve known for a long time that I want to marry you. I don’t want to wait for the sake of waiting anymore.” She said she felt the same.
They shopped for rings, and that December, Sheahan got down on one knee to propose in front of a Christmas tree at the Mansion on O Street.
“I think what makes it work is the fact that we can do anything or nothing and still have just as much fun,” Ramsey says.
The pair wanted the wedding to be an opportunity for their friends to become friends. They planned a series of events for the weekend after Thanksgiving, starting with a Friday night welcome party at the Mansion on O Street.
The next morning, Nov. 24, they exchanged vows before a bank of windows overlooking the Potomac River at Sequoia Restaurant. Guests sipped mimosas throughout the ceremony before dancing the afternoon away. That night everyone reconvened for an open bar and cover band at George, a bar in Georgetown.
Sheahan is grateful for Ramsey’s marathon dating challenge, although he remains astonished that she didn’t get scooped up by bachelors 1 through 28.
“She’s just an incredibly bright person. I can’t understand how any person at all could hang around this woman and not react the same way I did,” he says.