Loading
Loading
Loading
Loading
Loading
Loading

Jacqueline & Caleb

    Home
    Schedule
leaf

Caleb Hildebrand

and

Jacqueline Hogan

October 3, 2025

West Point, NY
101 days101 d1 hour1 h10 minutes10 min19 seconds19 s

How We Met

First Met to First Date

We first met at Mount Saint Mary College (our undergrad) at a party while dating other people. Looking back now, that first night we both said "Wow I wish they were single!" Anyway, a few years passed, and we did not know that we were both finally single. However, I had got some courage and decided to randomly Snapchat him one night, which was the start of our journey. On our first date, we met in the middle since he lived in CT and I lived in NY. We went to Tarrywile Mansion Park and walked around for hours just talking and trying to find this castle, I think we even circled the pond twice. Eventually after reading some signs, we found out it was actually across the street from the park! We did go inside this abandoned castle that was probably not the safest but it added to the adventure. We then went to the Danbury Mall and he taught or I should say TRIED to teach me stick shift. We ended the date the best way by going to get ice cream. We now are living together in NY and cannot wait to take the next steps in our life journey together.

The Proposal

05.04.24

I planned on proposing to Jacqueline when all our friends visited to go to a winery. Somehow, she figured it out so I decided to do it a week earlier for her birthday dinner, at Lake View House in Newburgh. While her brother and sister-in-law were taking pictures, I started the proposal. I looked at her and said, "I wasn't honest with you this morning. I do have another birthday present for you." She was so surprised that she thought I was joking and asked her brother, "Is this for real?" Once I took the ring out, she realized this was for real and said "Yes!” Her parents arrived and they gave their congratulations. Before the proposal, I had spoken with her mom, Kelly, about adding my parents to the dinner reservation, which was the final surprise for Jac that day. When my parents arrived we were all smiles. It was the first time my parents got to see the ring in person. Jacqueline was positively glowing showing it off. The ring looked beyond perfect on her. After many congratulations and pictures taken, we finally found our way to eat dinner. The best way to celebrate an engagement is a meal with family.

For all the days along the way
About ZolaGuest FAQsOrder statussupport@zola.com1 (408) 657-ZOLA
Start your wedding website© 2025 Zola, Inc. All rights reserved. Accessibility / Privacy / Terms