
How To Plan Live Music for NYC Proposal
If you follow Music Dept, you already know that we LOVE surprise performances! Late in March 2021 we got a call from a gentleman planning a very special proposal and wanting to incorporate live music. It’s always great to help clients brainstorm and explore different options, but this guy knew exactly what he wanted-an incredible singer/guitarist to perform “Can’t Help Falling in Love” moments before he proposes to his girlfriend! He also referenced the version from Crazy Rich Asians.
ALL PHOTOS From Jenna Cavanaugh, Wedding and Elopement Photographer

I immediately thought of Sandra Small. Her strong and beautiful voice and rock solid guitar chops would be the perfect for this brief and impactful moment of music. Sandra even recorded a rough-demo of herself singing the song so that our client could get a feel for her sound.
With any surprise performance, planning, flexibility, and teamwork are essential. We made small adjustments to timing and delayed by a day(due to weather.) The venue RH Rooftop allowed Sandra to stash her guitar out of site and blend into the crowd until the perfect moment. Jenna, the photographer, was also a tremendous help and we are so grateful to be able to share her incredible photos of the day. Definitely be sure to check her work out if you’re planning a wedding, proposal, or elopement.


How to Plan a Proposal with a Live Musician in New York City
- Pick the Location
NYC has so many incredible and romantic public spaces, but it’s important to remember that there are things in a public space that are beyond your control. It maybe noisy, crowded, or in rare occasions live music maybe prohibited. We know this landscape well and always educate our clients on the pros and cons of any location. Although the majority of our proposal performances do take place in iconic public spaces(Central Park, Brooklyn Bridge, etc) we’ve had some great ones in private spaces like restaurants, venues, and landmarks that must be reserved.
- Pick the Song & Performer
These steps could seem interchangeable, but some songs and performers or bands would work better in some locations than others. This sort of song selection is always a special request and our musicians love to learn and perform new songs for proposals. Because live music for a wedding proposal is such a powerful and laser focused moment we typically have the performer record a short demo of the specific song-this way the client knows exactly what it will sound like.
- Coordinate the Logistics
It can be tricky to coordinate a surprise performance, so we always suggest having a call with one of our coordinators to go into detail. Sometimes the person proposing wants to be walking along together and then come upon a performer and other times they will wait with the performer and the significant other will come upon them. It can also be stressful if the person proposing is the musician’s only contact. So, if you’re going to have anyone else around, like a close friend or hired photographer, its a great idea to make this person the musician’s contact.