How an iPhone App Lead VC Jason Pressman To Make A Huge Romantic Gesture For His Girlfriend

Shasta Ventures VC Jason Pressman is a newlywed, married to Jessica Newman (now Jessica Pressman).

How he got her to say yes is really one of the sweetest stories we’ve heard in a long time.

It all started with an iPhone app called the Tiffany Ring Finder from legendary jeweler Tiffany & Co, Pressman told Business Insider. The app lets you shop for rings and see what they’ll look like on your hand.

His girlfriend couldn’t decide between two rings. Pressman let her believe the decision to ask for her hand was still up in the air when he booked a trip to a tropical island.

On the first night there, he got down on one knee and presented her with one of the rings she loved. She said yes.

Then on the second night, he proposed again, this time with the second ring. Dumbfounded, she said yes again.

And here’s where it gets really sweet. On the third night, she discovered another box hidden among their things. It wasn’t another ring, he told her, he’d already given her two, which even he knew was over the top, and she wasn’t a big jewelry lover to begin with.

This time, in the box was a little gold charm, the letter “P.”

With her maiden name, the two of them had nearly the same initials, hers were JMN and his were JMP. She had made a joke some time ago that if she ever married him, she could almost still keep wearing her favourite piece of jewelry, a charm necklace of her initials, if it weren’t for the letter P.  So he solved that, for her, too.

Here’s a picture of the happy couple and the first ring, moments after she said yes.

Jason PressmanJason and Jessica Pressman and the first ring

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