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 Barcelona? From hilltop views to GaudĂ landmarks to the Gothic Quarter. 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.
Planning a proposal in Santorini? Oia, the water, and locations away from the crowds. Where to propose, eat, and stay.
Planning a proposal in New Orleans? The Mississippi, City Park, and the French Quarter. Where to propose, eat, and stay.
Proposal Advice
All adviceA 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.
You've picked the ring. Have you picked the right moment in the relationship? The questions worth sitting with before you propose.
Should you ask her father before proposing? The tradition still has defenders. Whether it works depends on who she is, not what year it is.
Just Engaged
Wedding Articles
All wedding articlesNewly 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.
The venue has three dates. Your family wants summer. She wants spring. How to set a wedding date when everyone has an opinion, including you.
A good wedding planner pays for herself. A bad one doesn't. What to look for, and whether you need one.
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