Hire a NYC Caricature Artist for Your Marriage Proposal

Surprise Caricature Marriage Proposal on Long Island NY

Caricature Marriage Proposals

Super-fun and super-romantic, my caricature marriage proposals have had a 100% surprise, success and satisfaction rate.

Posing as a caricaturist who “just happened to be nearby,” I work with locals and far-flung New York City visitors, capturing their moment in a lasting keepsake at charming locations around NYC and Long Island.

Reactions have been priceless and so is the value of this seemingly spontaneous yet very well-planned approach to popping the question. And the afterglow? In spades. Joe Vissichelli, Caricature Cupid!

Where Clients Have “Popped The Question”

It sounds so easy, right? You would think that surprise marriage proposals are a piece of cake. But proposals in public settings can require improvisation when things vary from the plan. And if it could seem fishy that a caricaturist has crossed the path of you and your loved one, my knack for banter and off-the-cuff humor will quickly put suspicion to rest.

Not everyone can do this. From my many years of drawing publicly and managing crowds, I know how to change the script and staging naturally so your future spouse will never guess what’s coming and you won’t miss your one special chance for an extra-memorable moment.

Your romantic New York City metro locations await! Some of the places I’ve performed caricature marriage proposals include:

Belvedere Castle in Central Park

The Empire State Building

Bow Bridge Central Park

Pulitzer Fountain at NYC’s Plaza Hotel

Azalea Bridge in Central Park

Brooklyn Bridge

Central Park’s Bethesda Fountain

Long Island & NYC Area Restaurants

What My Marriage Proposal Clients Say

Slide Orchestrating a surprise proposal in Central Park from across the pond was a daunting prospect, but Joe with his wealth of experience, wit and relaxed character made it a walk in the park. T. Edwards, Groom-to-Be Slide The caricature was perfect, and it was the perfect way to surprise her. I could not have been happier from start to finish! You were GREAT! R. Sprague, Groom-to-be Slide The day of, my fiancé didn’t expect anything once Joe came up to us asking us if we wanted a caricature. It was truly the perfect day! M. Alessi, Groom-to-be Slide I would 100% recommend Joe to anyone out there who's looking for his services for a surprise proposal (or any occasion for that matter)!!! A. Pham, Groom-to-be Slide Being halfway around the world, Joe was very professional and accommodating with all of my requests and someone that you can definitely trust. A. Pham, Groom-to-be Slide You are a man of your word. Your work is outstanding! I couldn't be happier! D. Perscetelli, Groom To Be Slide It went exactly as planned. She didn't know it was coming at all and was very stunned. She said yes, of course. It turned out to be a very memorable night. Thanks again for your help!! B. Ishkalov, Groom To Be Slide Thank you so much for helping me with the engagement. Your expertise was a key part in making one of the most important days of my life flow smooth and flawless. R. Sprague, Groom To Be Slide I had Joe do my “secret” proposal at Central Park – and it was amazing! He worked with me for a while prior to the actual engagement day, to make sure that the final caricature was exactly what I wanted. M. Alessi, Groom to Be Slide I had contacted Joe with the idea of a surprise proposal and he was an absolute pleasure to work with from day 1. The drawing was beautiful and will be something that Melissa and I will forever cherish. A. Pham, Groom To Be Slide Thank you so much for today, it was perfect! She was so in shock and baffled it was amazing! The picture is amazing! We will frame it and hang in our home!! A. Davis, Groom To Be Book NY Caricature Entertainer

Frequently Asked Questions

Rather than take chances with your special moment, I create the art before your proposal from your photos, bring it to the site and, after approaching you as a “nearby” caricature artist, I draw a “token” caricature for five minutes of banter and fun before handing over the pre-finished art for the big climax.
Major life moments like this are simply too important to mess up. My working method gives you more control of the finished product and greatly reduces the chances of several problems that could ruin the day.
First, by not drawing you proposing on the spot, no passersby can react out loud and tip off your loved one, ruining our plan. This has happened to other artists. If weather becomes an issue, we can quickly switch to a safer location but you can still have your preferred scenery in the artwork. You’ll also more easily control the art’s final look because you’ll see a preliminary sketch that I can revise if you so desire. Lastly, even the best caricaturists can have a bad moment, but by getting a drawing you’ve already approved, the “hit-or-miss” nature of quicksketch caricature is eliminated and your surprise artwork won’t be an unpleasant shock.
The final art is 11″ x 14″ and the artwork is executed in marker with rubbed-in chalk for color. Other sizes and modes may be available upon request.
Besides my expert advice and consultation, you’ll get an emailed sketch I can revise to your liking if necessary, full color final artwork, an emailed digital file for safekeeping, lest your original be someday lost or damaged, and finally, the in-person “performance” itself. Works like a charm

What is the Price for Caricature Artist Marriage Proposals?

With prices starting at $595, my caricature proposals include a sketch for your approval, a round of revisions (if desired), final caricature art in both digital and physical formats, and meeting you locally in much of New York City or Long Island for the “performance” itself. Additional fees may apply for travel to other areas and special requests.

If you’d also like to have photographic and video keepsakes to capture your proposal moment and celebrate your engagement, I also work with other New York professionals. I will be happy to provide you with referrals and suggestions.

How To Arrange Your Surprise Marriage Proposal

There are three easy ways to make arrangements:

1. Call me today at 516-593-4844

2. Email me: joe@caricaturedreams.com


If you know your marriage proposal date, time and location, please provide the information so I can provide an accurate quote and account of my availability. If you don’t know and need help with ideas and logistics, I am here to help you plan your special proposal.

Let’s get started today!

Creative Central Park Marriage Proposal Artist at NYC's Belvedere Castle

Setting Up a Surprise Caricature Marriage Proposal