Planning a proposal in Chicago? From the Wrigley Building on the river to the Skydeck at the Willis Tower. Where to propose, eat, and stay.
Proposal Ideas, Location Guides, and Real Engagement Stories

For the proposal itself
Get Engaged
Where to do it, what to say, and how to pull off the moment without giving it away.

For after they said yes
Just Engaged
Picking the date, selecting your wedding party, setting a budget. The list that starts the moment you stand up.
Get Engaged
Where to Propose
All location guidesPlanning a proposal in Paris? From the top of the Eiffel Tower to a bridge over the Seine. Where to propose, eat, and stay.
Planning a proposal in Prague? From the Charles Bridge to the gardens of Petrin Hill. Where to propose, eat, and stay.
Planning a proposal in Las Vegas? The Strip, mid-air adrenaline options, and spots outside the city in Red Rock Canyon. Where to propose, eat, and stay.
Planning a proposal in New York? The Empire State Building, Central Park, and Tiffany's on Fifth Avenue. Where to propose, eat, and stay.
Proposal Advice
All adviceShe's already talking about the honeymoon. She has opinions on ring styles. Ten signs she's been waiting longer than you think.
Planning a surprise proposal with a girlfriend who notices everything. Seven tips for keeping it secret from the ring purchase to the night itself.
A public proposal is either the best story she'll tell for years, or the worst. What to think through before you commit to an audience.
Just Engaged
Wedding Articles
All wedding articlesBarn or ballroom? Beach or city hall? Settling on a wedding style that fits both of you takes longer than most couples expect.
A destination wedding sounds perfect until the guest list drops to twenty. The tradeoffs that matter, from costs to family politics.
Newly engaged. Tell her parents before it hits Instagram. The order matters, the timing matters, and getting it wrong is harder to undo than you'd think.
Choosing the Ring
Choosing an engagement ring? The 4Cs, setting styles, metal choices, and how to figure out her ring size. Everything before you walk into a jeweller.
Read the ring guide