Dating Profile Photos in Chicago: What a Professional Dating Photography Session Is Really Like

Yes, this is a real thing. Yes, I really do it. And yes...it works.

I'm Emily, a portrait photographer based in downtown Naperville, and dating photography is one of my favorite things I offer. Partly because almost no one else does it, and partly because the results genuinely change things for people. Not in a cheesy way. In a "I matched with someone who actually recognized me at the restaurant" way.

Why your current dating photos aren't working

Let me guess what's on your profile right now: one mirror selfie, one group photo where nobody can tell which person you are, one picture from a wedding in 2019, and possibly a fish.

Here's the problem. The apps are a split-second visual decision, and photos that are blurry, dark, or several years old read as "this person isn't really trying." You ARE trying. Your photos just aren't saying it.

The goal isn't more matches. It's the right ones.

This is where my approach is different. I am not trying to make you look like a stranger... that strategy collapses the second you show up to coffee. The goal is you, on your genuinely best day, photographed in a way that shows who you are and what your life actually looks like. The coffee shop person. The lives-for-the-lakefront person. The reads-actual-books person.

We build a little strategy before we ever shoot: who are you hoping to attract, what does your real life look like, and how do we show that honestly? Then the photos do the filtering for you.

What the session is actually like

We shoot on location in downtown Chicago or downtown Naperville... walking, talking, coffee in hand. Nothing staged against a backdrop. I coach you through every single frame, so if the words "I'm so awkward in front of a camera" just went through your head: I know. Everyone says that. So am I! I got you.

You'll leave with a set of natural, current, genuinely-you photos sized and ready for the apps.

Frequently asked questions

Is a dating photo session awkward?

For about four minutes. Then we're just two people wandering the city while one of them happens to be holding a camera.

Will people be able to tell my photos are professional?

They'll be able to tell they're GOOD. We shoot candid-style, outdoors, in real light. No studio backdrop, no corporate headshot energy.

Do men book dating photography sessions?

Constantly. Honestly, men's profiles benefit the most, because the photo bar out there is... low.

How many dating profile photos do I need?

Four to six strong, varied images beat twenty mediocre ones every single time. We'll get you well past that in one session.

Ready to stop losing to bad lighting? Call or text 312.600.5151 or email emily@emilycummingsphotography.com. I'm based at Studio 25, 25 W. Jefferson Ave in downtown Naperville, and I shoot dating sessions in both Naperville and Chicago.