Coach proposes in front of team
STEVENSVILLE — It was a storybook proposal when lacrosse coach Bobby Woolley, Crystal Callahan’s boyfriend of three years, popped the question in front of his entire team.
May 30 happened to be her first day off in eight days, Callahan said. She had an appointment to get her hair done, then texted Woolley to see if he wanted to go to Annapolis to get pedicures together.
“So, we get our toes done, and he says, ‘ Hey, just get your fingernails done, as well, while I run to Sam’s Club for the businesses, and I’ll just pick you up,’” Callahan said.
Wooley often has her hair and nails done, so she didn’t think anything of it.
After she got home, she said she cleaned the house, took Bella, their dog, for a walk, answered a few emails, took a nap and woke up to get ready for the end of the season lacrosse banquet at the Kent Island American Legion. Woolley is the head coach of the Kent Island High School boys lacrosse varsity team.
At the end of the banquet, all the coaches thank their wives or girlfriends for supporting them, so she wasn’t surprised to see Wooley up on stage and hear him talking about how supportive she is and how much he cares for her. Behind him was a slide show playing pictures of the two of them.
The team mom leaned over and told her, “He got you flowers; go up there.”
Then Woolley said, “Babe, come see me on stage.”
As she went to the stage, Callahan said she still had no idea he was going to propose. But when she turned around, looked out across the crowd and saw her entire family — mom, dad, brother and sister — off to the side of the room, she said she instantly knew.
“I immediately lost it, crying with happiness and joy,” Callahan said.
Woolley got down on one knee and asked her to marry him.
“Of course, I said, ‘Yes’!” she said.
The crowd cheered.
“I cannot wait to marry my best friend, my rock, my life partner, my forever dance partner, my forever date, my soulmate,” she said.
Callahan is the daughter of Jay and Linda Callahan of Chestertown. Their family name formerly was Pippin, but they changed it a few years ago when her dad Jay found his biological father, she said.
She worked as an orthodontist technician for 12 years but left that and now is working a couple part-time jobs.
Woolley is the son of Brenda Baker and Robert Woolley Jr. of Kent Island. In addition to coaching, he runs a couple local businesses.
“We’re excited,” she said, and Woolley’s romantic nature is continuing. “He keeps adding things (for the wedding), like a horse and carriage.”
A June 2019 wedding is planed at a private residence in Wye Mills.
Bobby Woolley, left, asks Crystal Callahan to marry him in front of his fellow coaches and lacrosse team at the Kent Island American Legion.
Bobby Woolley and Crystal Callahan are engaged to be wed. A June 2019 wedding is planned.