Mila Lowe


Say Yes: Michael & Caroline

A cliffside surprise.

Just like in the movies, Michael McMillan II’s life seemed to move in slow motion the second he locked eyes with Caroline Hubbard as she entered a San Francisco bar. He was on his way out, but it was love at first sight in its truest form, so he had to introduce himself.

The couple dated for more than five years, so by 2021, Michael was more than ready to propose. He wanted to pop the question on Martha’s Vineyard because the Island was where he first met Caroline’s family. That August, the couple took a vacation to the Vineyard and at the end of the week, Michael drove Caroline to the Gay Head Cliffs under the guise of a surprise dinner. Meanwhile, he had secretly arranged for Island photographer Mila Lowe to capture the once-in-a-lifetime moment.

“Once in position, I expressed my love for her and commitment to her and took a knee. After presenting the ring, I made the request for Caroline to be my wife; she burst into such earnest crying that the emotions masked her answer, leaving me – to this day – to assume it was a ‘Yes!’”

They embraced and were joined on the beach moments later by their families, who had been hiding nearby. The evening concluded with joyous celebrations under a picturesque sunset at the Outermost Inn. An August 2022 wedding is planned in Austin, Texas, where the couple resides.

Comments (1)

John Arrington
Oak Bluffs, MA
Can’t wait to fly out to Austin for the Wedding! Congrats to Caroline and Michael.
July 29, 2022 - 12:18pm