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Awe, Snap!

Carasco, Chicago’s go-to wedding photographer for pics with big personality, weighs in with tips and tricks for stunning engagement sessions.

By Elise Hofer Shaw

Cara and Scott Nava, the husband-and-wife dream team behind Carasco Creative Photo & Video, have been capturing chic Chicagoland weddings for more than 17 years. And they’re in high demand for shooting surprise engagements, too. Here, Cara answers our burning questions about all things engagement photography—and shares her sage advice on everything from tips for how to pull off a passionate proposal to input on best practices for popping the question during a pandemic.

Imitation is the sincerest form of flattery. What are a few examples of some of the most creative (and sentimental, natch) ways you’ve seen Chicago couples pop the question?

CN: One of the cutest pre-COVID ideas we have seen incorporated a street caricaturist with a sketched picture of the couple. There were word bubbles that said, “Will you marry me?” Thinking of going really big? Whether it’s a grand gesture such as flying in an internationally acclaimed violinist for a private performance or orchestrating an epic proposal overlooking the Cliffs of Moher in Ireland, the sky's the limit for ways to pop the question. But remember, it doesn’t have to be over-the-top (or expensive) to be sentimental. Your idyllic landscape for a proposal spot could be as simple as the restaurant where you had your first date! At the end of the day, whether you opt for an intimate lakefront proposal or invest in a destination trip to pop the question, finding what is meaningful to you as a couple—and carefully curating the logistics—is the true key to getting great proposal photos.

What is your advice for capturing engagements during COVID? And what are some of the adjustments you’ve had to make?

CN: Wide open outdoor spaces are the best option for engagement shoots during COVID. As the entire world has had to adjust, we, too, have to keep social distancing in mind while photographing couples. Fortunately, we have a range of lenses that allow us to zoom in and keep our distance from the subjects. Honestly, the biggest adjustment—besides location availability (read: not being able to shoot indoors as much)—is the social/psychological element. We tend to build tight relationships with our clients, so it’s strange to not be able to go in for a hug to say hello or goodbye.

It’s chilly or downright cold in Chicago basically eight months out of the year. What are your engagement timing tips for fall/winter photo shoots?

CN: Most of our engagement shoots in Chicago take place before December in order to take advantage of the milder weather. And for those who envision a winter wonderland-style shoot, they often do a “mini session” (a quick 30-minute session) and then a second, full session on a warmer day. But if it’s a winter shoot you’re set on, don’t be afraid to go for it! Just bundle up and embrace the season. Moderate winter accessories like a long jacket or mittens can enhance the look of the shoot. But keep in mind that fashion is a balance of practicality and aesthetics. Visibly, it makes sense to wear a sweater or coat if there’s snow on the ground. However, too many layers may give a bulky appearance. As for winter backdrops, snow-capped trees can be epic for engagement photos. However, extreme elements such as wind and sleet can create unwanted obstacles and discomfort during the shoot. If clients are uncomfortable, the success of the shoot unravels very quickly. In short, flexible planning produces the best results.

For the partner who’s doing the proposing—and wants to make sure all is documented from the surprise to the posed photos après ask, what advice can you give?

CN: Glad you asked! Here are some finer points to consider…

1. Ask for a “blessing” and record the occasion (even if it’s via Zoom). Of course, this is completely based on your comfort level and relationship with your significant other’s family. But asking a parent (or other parental figure) for their son or daughter’s hand in marriage is a beautiful moment that you might want as a memorable keepsake for you and your family.

2. Budget for and hire a photographer to document the occasion—and plan to spend at least another 15-30 minutes taking photos after the proposal goes down.

3. If your budget allows, I recommend hiring an experienced proposal planner. The more elaborate the proposal, the more elements and logistics that need to be curated. They can assist with creating a visual focal point and sourcing design vendors (such as floral design, signage, etc.) and in making sure the photographer knows where to be and when so that you aren’t busy texting—and potentially blowing your cover.

4. Select a sentimental or idyllic location, keeping your future fiancé in mind. Is there a first date spot or a tradition that you share? It really is the thought that counts.

5. Treat him or her to a manicure. Your partner will want to show off their new bling in photos—professional pics and IG snaps—so eliminate the worry for them and make sure their hands and nails look polished.

6. Plan an “after” celebration—a dinner with friends and/or family so there’s a reason for him or her to dress up. If you are so inclined, you can plan a surprise engagement party or keep it simple and celebrate with just the two of you. Either way, you will want to have celebratory plans for later that evening.

7. Beyond the aesthetics of the location, consider the logistics and optics of your proposal backdrop. For example, do you want a specific cityscape angle in the background? Discuss that with the photographer and have a plan on how to orchestrate the shoot. The main thing is coordinating the moment so that the photographer can document the actual proposal reactions. The rest of the photos can be staged once he or she says yes.

What are your favorite locations around town for fall photo shoots?

CN: From the golden fall foliage to cozy outfits, autumn engagement sessions can incorporate the warm-and-fuzzy seasonal details that we all love. With its ombre leaf colors and a classic bridge view of the city, the Lincoln Park South Pond area is tried and true for being really lovely this time of year. We also love the Art Institute of Chicago for fall engagement shoots. It’s a brilliant location for indoor photos because of the striking archways, clean lines, geometric shapes and glorious natural light. And the AIC’s surrounding gardens offer a spectacular canopy of honey-hued locust trees with an iconic sculptural fountain at the heart of the garden. It’s truly one of the most beautiful landscapes in Chicago.

What are your favorite locations around town for winter engagement shoots?

CN: When the Wrigley Building area is lit up for the holidays it can make for a dreamy ethereal look thanks to all of the twinkling lights in the background. Also, Water Tower Place has beautiful layering for an iconic Chicago seasonal portrait because of the nearby street lamps and illuminated trees.

In terms of getting the most out of your engagement photos... Is there anything else couples can plan ahead of time to ensure their pics are stellar?

CN: 100 percent. Here are some additional things to think about…

1. Communication: As photographers, we want to know how you really feel. Seriously, we do. We want to know if you like fun lifestyle photos of yourselves laughing, editorial-style photos or something in-between. If you don’t like your “closed lip” smile, mention it to your photographer. If you aren’t into kissing photos, tell us! Every couple is different, and photographers don’t want to assume anything.

2. Have a backup plan: Are you in a crunch for save-the-date photos? Consider an indoor location that offers “photo permits” to photograph in their space (fees vary by location and duration). That way, if the weather is bad, you’re guaranteed to get the photos you need.

3. Plan your wardrobe: In terms of wardrobe, it’s important for the couple’s style to shine through. Avoid wearing anything that will be uncomfortable to walk around in for over an hour. The more comfortable a couple is, the easier it will be to capture them in the moment. If you want two outfits, you’ll want to make sure that you are planning ahead for somewhere to change clothes, and be sure that the session you booked allows for that clothing change.

4. Consider your fiancé/fiancée’s attire: If one person is donning a cocktail dress and high-heel Valentino’s, casual shoes and an oxford shirt are probably a bad idea for the other person. Your outfits don’t have to match exactly in color but should complement each other in style.

5. Trust your photographer and have fun: Building a relationship with your photographer is key. Once you’ve communicated all of your concerns and your goals for the photos, trust your photographer and have fun while you are on the shoot. As photographers, we play on the couple’s behavior and capture the love, emotion and humor. Worry less about the camera and think about it as a date (but with a camera pointed at you—ha!).

Safety is a two-way street. Behaviorally speaking, how can couples respectfully interact with their photographer(s) to keep you safe, too?

It is preferred if couples wear masks when we first meet up for the shoot. Beyond that, limiting physical contact is best to ensure that we are taking as many precautions as possible.


Too many options can be overwhelming, especially with all of those “The Best Wedding Venues” hotlists floating around out there. Well fret no further… The team at Chicago Loft Venues is here to help you narrow your search and spread out your budget where it counts. Reach out to Creative Director Joshua Yates at events@chicagoloftvenues.com for ideas on how to slay the planning process from day one.

For more info on how Carasco can capture your engagement, big day and beyond, visit carascophoto.com.

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