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7 Things You’ll Regret Not Asking Your Wedding Photographer

Couple posing in the solarium at the Tinsmith Madison.

February 8, 2023

I’m Liz
As a former ICU nurse, I know what it’s like to be in high-stress situations. In fact, it’s where I thrive. I would love to bring my calm to the natural chaos that comes with planning your wedding. 
About Me

Introducing the first of our guest vendor features: Wisconsin Wedding Photographer Olivia of O & B Photo Co telling you exactly what you will regret NOT asking your wedding photographer.

Ps- The very first event Dream Weddings + O & B Photo Co worked together was published in Green Wedding Shoes – This Bride Wore A Pink Wedding Dress For Her Colorful Greenhouse Wedding


Oh hiii!! Olivia with O & B Photo Co here! Raisin is curled up like a little fox, and snoring in the patch of sunshine in my office. My coffee is piping hot, Schittt’s Creek is softly playing somewhere in the background, and my vibe is “ready to share some no b.s. tea with y’all”. 

I’ve been photographing weddings nationwide with my husband Bryan for the past 7 years. 

Are our tummies full of wedding cupcakes? Oh yea. Have we pet all the doggy ring bearers? You better believe it. Have we seen every type of venue, situation, and wedding day you could possibly think of? FOR SURE.

That’s why I’m here to share what we’ve seen and how asking the right questions can get you the wedding experience that you deserve. No b.s. 

Can you light my dark reception? 

Whether you have a windowless getting ready space, evening ceremony, or a dark reception space, you need to know how your photographer will approach these situations and ensure that your photos turn out properly. Some photographers prefer all natural light, in which case they might not be the best fit for an after-dark ceremony. Other photographers, like us at O & B Photo Co, bring our full lighting kit with us. This means that whether it’s 9am or 9pm, your photographer is confident in fully lighting any space. 

When can I expect my finished gallery?

If you polled 10 different photographers, they’d likely have 10 different photo gallery delivery timeframes. Backing up your images, editing, and retouching all take time and each photographer has a different process for these things. This straightforward question will help you understand which date on the calendar you should circle in a big red heart. A range of 4 weeks- 12 weeks post wedding day is what you’ll see on average across the wedding photography industry. 

We’re a fan of no surprises (unless it involves birthday cake or winning a TJ Maxx shopping spree) and are taking a guess that you are too. Ask your photographer and read your contract! 

What is the role of your second photographer?

Full transparency – this is one of THE MOST IMPORTANT questions you can ask. It directly affects your wedding day timeline. Here’s why.

A second photographer is most commonly considered supplemental. That means they are there for all the same things that the lead photographer is present for, but are simply shooting from a different angle. For example, if the main photographer is at the head of the aisle capturing Partner A walking down the aisle, the second photographer will be stationed at the back to capturing Partner B’s reaction to seeing Partner A. With a supplemental second photographer approach,  you will need more time in your wedding day timeline to accommodate for the lead photographer to capture each wedding party separately as well as the full party together, as the lead and second photographers will not be shooting apart from each other. 

However, some photographers utilize a second photographer almost as a second lead! For us at O & B Photo Co., we’re a husband and wife team. While Olivia captures the bride and party getting ready in the Iron Horse Hotel, having a bridal party first look, and hitting the town with bottles of champagne to spray in the Third Ward, Bryan captures the groom and party getting ready in the Kimpton Journeyman Hotel, toasting to the day’s festivities, and hopping in the party bus to swing by Lakeshore State Park for groom’s party photos. We very much are separate as leads until we’re reunited. 

Having a clear understanding of exactly how a second photographer is utilized will directly influence how long it will take for certain portions of the day to be captured. Thus paying a factor in your wedding day schedule. 

What happens if you have an emergency? 

Of course your photographer will do everything in their power to ensure this doesn’t happen. But in the very off chance that it does, you’ll want to make sure that you’re hiring an established photographer. Aka someone who knows lots of fellow talented photographers and has a network of  professionals. If an emergency were to occur, your photographer ideally should be able to reach out to their network, find an associate with a similar level of experience/shooting style, and have them step in to photograph. In this scenario, a different photographer would be photographing but the original photographer would still be editing your final images to their signature artistic style that you know and love. 

If for any reason your photographer cannot find a suitable associate to fill their shoes on the day of, a refund should be given. Your contract should outline exactly what this emergency process would look like. It will also outline how much of a refund would be given in the extra unlikely situation of not being able to find an appropriate associate.

Where would you like to be seated for dinner?

Let’s spill the tea here. No one wants photos taken of them shoveling spoonfuls of mashed potatoes in their mouth. BUT, you DO want photos of your loved ones giving speeches. The closer you seat your photographer to the head table, the better your kissing and speech photos will be. Why?

1- We’ll eat at or close to the same time as the head table. Nothing is happening (speeches, mingling, etc) when the wedding party is eating. However, by the time the middle to back tables of guests begin to get their food, your best man is already starting his speech. If we aren’t sitting up front, we won’t be able to eat the food that you paid for us to eat before staff takes it away and dancing begins. And let’s be real, does anyone want their lunch break cut short?!

2- I’m a photographer with two cameras around my neck, not Usain Bolt. Put us in the farthest table in the darkest corner of the room and we’ll be running at breakneck speed and leaping over Grandma Lucy’s cane in an attempt to capture your mid-dinner, glass-clinking kiss, only to miss it. It’s just not a realistic expectation to put on a person.

Your photos will be directly impacted by when and where your photographer eats. 

How much time should I a lot for posed photos? 

Your wedding day timeline is largely dictated by how much time you need for your photos! We’re incredibly meticulous about ensuring that there is ample time to capture what needs to be captured AND having some flex time. This means that even when (not if- it’s a wedding day, baby) things run behind, we can roll with it and everything will still go on without a hitch. 

Here’s our suggested timings for group photos

  • 1 hour for newlywed portraits
  • 45 – 60 minutes for wedding party photos
  • 30-45 minutes for around 12-15 groupings of family formals 

And here is what that looks like in an actual timeline that we worked up for one of our couples.

  • 12pm O & B Photo Co arrives and photographs details/getting ready
  • 1:30pm Bride gets into dress (Olivia photographing); Groom gets into suit (Bryan photographing)
  • 2pm First look and newlywed portraits
  • 3pm Wedding Party photos
    • Separate parties and all together
  • 4pm Family formals
  • 5pm Ceremony
  • 6:30pm Dinner


Moral of the story, ALWAYS allow more time than you’d think. 

What is the one thing you’ve seen make or break a wedding day? 

Your photographer has seen more wedding day’s than a normal person will ever see in their entire life. Which means they’ve seen what can go wrong and what does go right. Truly take time to hear what their answer is; it will only benefit you. 

O & B Photo Co’s answer, hands down, is *drum roll*…….A WEDDING PLANNER. Nope, not just a day of coordinator. The difference between weddings where our couples utilize a full service wedding planner and do not is dramatically noticeable. Not just within the stress levels of the couple but how the actual day plays out. 

This past weekend, the wedding planner shined the bride’s ring for detail photos, worked with the hotel to block of different spaces for us to do first look and family formals, drove the veil to the bride during the middle of wedding party photos, and helped wrangle rowdy family for large group photos. And that’s just what they did for US. Here’s what they’ll do for YOU. 

When we worked with Liz for a color explosion themed wedding at The Tinsmith, she ironed out exactly when each vendor would arrive, what the expectations were for each vendor were, ensured that tables were set to the couple’s vision, carried an emergency kit of things like a sewing set, stain sticks, deodorant, worked up the entire timeline for rehearsal day and wedding day. She ironed out all of the details like who would be doing what and when, and she did it in a timely way to ensure there was no last minute happenings. We witnessed the wedding party and family actually have down time to sit and talk and even visit a favorite bar for a pre ceremony drink. In 7 years of photographing as a team, we  have never witnessed this happening without a full service wedding planner. 

You should enjoy your wedding, not be consumed by stress and planning. Life is short. Get the planner (specifically Liz. She’s next level.)

If you want to learn more about Olivia and Brian, the amazing photographers behind O & B look here!

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