Oliver’s friend didn’t have the final episode, but knew that her buddy Jake Kohlman recorded it, so the two women hopped in a cab to his apartment. Kohlman, a reserved 25-year-old Washington native who worked for a union, was taken aback by Oliver, who spent the whole night telling him what to do. “Pause it here,” she said more than once during the episode. “Let me cry here.”
Oliver didn’t think much of the interaction, but when she saw Kohlman two weeks later at an Adams Morgan bar where he worked, she was so happy to see a familiar face that she hugged him.
Oliver wasn’t sure what shifted for her that night but after a couple of glasses of wine, she returned to Kohlman. “Will you be my Derek?” she asked, referring to the “Grey’s Anatomy” heartthrob. “And I’ll be your Meredith.”
Kohlman didn’t know how to respond, but when Oliver asked if he had a bed she could sleep in that night, explaining that she’d spent two weeks on her friend’s floor, he gave her his phone number. But Oliver ended up back at her friend’s place and the next morning she texted Kohlman. “Is it weird that I’m disappointed that I didn’t wake up next to you?” she wrote.
“Actually, me too,” he replied.
Oliver assumed that meant the crush was mutual, but then nothing happened. They would meet at bars with friends and chat online during the day. They even kissed on St. Patrick’s Day, but for months Kohlman never asked Oliver out or made the next move.
“I tend to go a little slower in relationships,” Kohlman says. “All of a sudden a tiny little blond person started disrupting my life. Not in a bad way. It just seemed like she was going to be involved in my life unexpectedly, but for a very long time.
In April he called and asked if she’d like to go to dinner. Oliver styled her hair and brushed on a fresh coat of makeup, and then was surprised when Kohlman drove her to California Tortilla for burritos. Still, they sat outside and talked for hours.
When her school year ended six weeks later, he invited her to celebrate with a fancier meal at Cafe Atlantico. They continued to see each other, but it was never clear where the relationship was headed.
Normally this would have driven Oliver mad. She’d always been quick to fall into serious romances. And since her father’s death when she was 19, she’d grown dependent on boyfriends and often felt anxious when they left even for a night.
But with Kohlman, she never worried.
“It always felt okay, which is weird,” she recalls. “He was making me be this person that isn’t depending on him to call me everyday, and I was okay if I didn’t see him every weekend.”