Tiffany and Ian

How They Asked

Our favorite restaurant in New York City is small restaurant in the West Village
called Little Owl. Two weeks prior to our engagement, Ian mentioned that we were
invited to an exclusive event at the Little Owl. I was slightly confused because he
mentioned we had to be there early (4:30pm). We got to the restaurant right before
they opened, but I just figured we were there early. The owner of the restaurant
(Theresa) unbeknownst to me, was in on the entire plan (as was the rest of the
restaurant). The restaurant has this adorable bench area which is perched above the
seating area and it only has two seats. The owner sat us there and brought us two
glasses of champagne. A few minutes later, they started playing this Ed Sheeran song
called “Perfect” which was ‘our’ song. Right when the song played, Ian got down on
one knee and said something in my ear and then popped the question with a ring in
hand. I was in complete shock and filled with so much joy and excitement. At this
point, the entire restaurant started going crazy for us and clapping, it was the most
magical moment, something I will never forget. Ian was smart enough to plant a Go
Pro camera on the shelve so the entire moment was captured on video and he also
hired a photographer to capture the evening.

She was great and got all the right shots of me crying Uncontrollably. It was perfect. After we took photos, we ate an amazing dinner. He then surprised me with a room at the four seasons downtown. It was Decorated with flowers, candles, sweatshirt with my new last name and tons of wedding goodies. After that Ian rented out a bar with all our friends and family to celebrate the engagement. The following day the two families went to Sarabeth’s to celebrate the engagement for brunch. It was The most perfect weekend and I couldn’t have asked for more. Every little detail and surprise was beyond amazing.

Tiffany's Proposal in Little Owl NYC

The photographer was great, she caught all the key moments, including my
uncontrollable emotional crying! After the ‘moment’ we ate an amazing dinner at
Little Owl and couldn’t stop smiling. After dinner, Ian told me we had to make a quick
detour before grabbing celebratory cocktails. Our car took us to the Four Seasons
Downtown – Ian got us a room for the night. We checked into our room which was
incredible, an amazing suite which he fully decorated with flowers, candles, and
clothes with my future last name and tons of wedding goodies. After a brief stop at
the hotel, Ian’s last surprise was celebratory drinks at the bar at Little Park, he rented
out the entire bar and my closest friends and family were there waiting. It was really
special and the most perfect evening – every detail was so thoughtful and planned
flawlessly. The following morning, Ian organized a brunch with both of our families at

Sarabeth’s in Tribeca. It was truly the most memorable weekend, I could not ask for
a more special weekend, I will never forget it.

Wedding Proposal Ideas in Little Owl NYC

Engagement Proposal Ideas in Little Owl NYC

Special Thanks

Steffi Chen
 | Photographer
Linda handsman and morgan handsman and hilda hayden
 | Planning
Michelle cummings
 | Planning