Grand Haven man pops the question on Olive Garden Pasta Passport trip

Posted at 4:35 PM, Jun 28, 2018
and last updated 2018-06-28 18:35:25-04

GRAND RAPIDS, Mich. - A West Michigan man's love for pasta, salad, and unlimited breadsticks led to a chain of events that's certain to warm your heart.

Jeff Gilleland knew he wanted his proposal to Samantha Roberts to be special.  As luck would have it, he won the trip of a lifetime and decided to take that as a sign to ask to spend a lifetime with Samantha.

Gilleland had two things to figure out before he could pop the question to then girlfriend Samantha Roberts.

“It just came down to a matter of ‘when,’ and ‘where,’” Jeff Gilleland said.  Those questions were answered when he won a Pasta Passport from Olive Garden.

When? April. Where? Italy.

“How much more perfect can it be? On a free trip to Italy, in one of the most beautiful places you’ve ever seen,” Gilleland said.

“I didn’t know he was going to propose on the trip.  I didn’t think he would, because there were so many people there. There were 50 winners, and everyone got to bring someone,” Samantha Roberts said. 

Turns out, Jeff was so excited to ask, it didn't matter who was around.

“He proposed in like the first 15 minutes of us being on site,” Samantha said. 

Photographers were on standby to capture the moment.

“They hid in the bushes for me. They all took pictures," Jeff said.

Those photos say it all.

“Right before he proposed, he said, 'we should do this forever', and I said 'what? Stay in Italy forever?'” 

While this couple can't spend forever in Italy, they are planning to spend forever together.

Sam and Jeff actually met on a blind date and plan to get married next September. As for the picking out the ring? Jeff says he studied Sam's Pinterest board for months.