Coach pro­poses in front of team

Record Observer - - Front Page - By AN­GELA PRICE bay­times@kibay­

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.

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