Chicago dating profile photography

Natural portraits that look like you on a very good day. Real light, real expressions, and a set of photos that gives someone a reason to say hello.

Check your dateSee sessions
Woman in a denim jacket laughing as she walks down a Chicago courtyard path, dating profile photography by Jeremy Glickstein

Six frames make a profile

Hinge, Tinder, Bumble, Raya, and most other apps show about six photos, and the order matters. Every session is planned around the set you actually need, starting with the one people see first.

  1. 1

    The first look

    A close portrait with soft light and real eye contact. This is the photo that earns the second one.

  2. 2

    Full length

    The whole outfit, the whole posture, somewhere in the city that suits you.

  3. 3

    Mid-laugh

    The warm, unguarded one. Usually it happens between the shots you planned.

  4. 4

    In motion

    Walking, a coffee in hand, a street you know. It reads as a moment, not a photo shoot.

  5. 5

    Your setting

    Architecture, a favorite café, a corner of Chicago that says something about you.

  6. 6

    The conversation starter

    One distinctive frame with a detail worth asking about.

You won't be told to just act natural

Before photography I spent ten years as an actor and acting coach, with a Steppenwolf Theatre Company credit and a Jeff Award. That work taught me why people freeze when a lens points at them, and how to get them past it.

So instead of handing you a pose and waiting, I give you something to do: walk to the corner, tell me about your week, react to something ridiculous. The expressions that come out of that are the ones that look like you.

Retouching stays light. Skin keeps its texture and you keep your face.

Sessions

The only real decision is how much variety you want. More time means more outfits, more settings, and more frames to choose from.

Session I

$850

About 1.25 hours

  • One outfit
  • One location: a street, park, or café
  • 4 to 5 edited images

A clean, focused refresh for the top of your profile.

Book Session I

Session II

$1,050

About 1.75 hours

  • Two to three outfits
  • Two nearby spots
  • 8 to 10 edited images

Covers all six frames, with extras to choose from.

Book Session II

Session III

$1,250

About 2.25 hours

  • Three to four outfits
  • Two distinct locations
  • 12 to 15 edited images

All six frames in two different looks, plus room to experiment.

Book Session III

Every session includes a short planning conversation about outfits and spots, sneak peeks within 48 hours, the full edited set the same week, and a personal license to use your images on dating apps and social media.

Where we shoot

Good light, clean backgrounds, and a setting that tells a little of your story. A few places that work well:

  • West LoopCoffee shops, warehouse brick, and Fulton Market's architecture
  • Wicker ParkMurals, cafés, and streets with character
  • The RiverwalkBridges, water, and the skyline overhead
  • Lincoln Park Nature BoardwalkGreenery with the skyline across the pond
  • Montrose HarborOpen sky and lake air, relaxed and wide
  • Somewhere that's yoursA favorite street or neighborhood spot. Tell me about it.

Questions

I'm awkward on camera. Will this work for me?

Yes. It is the most common thing people tell me before a session. You won't be posed and left standing there. You'll be walking, talking, and reacting, and the photos come from that.

Which apps are these photos for?

All of them. Every set is built for Hinge, Tinder, Bumble, Match, Raya, and The League, and works just as well on Grindr, HER, Feeld, BLK, Chispa, JSwipe, Jdate, Stir, OurTime, Christian Mingle, Coffee Meets Bagel, eharmony, OkCupid, and happn. Newer matchmaking apps like Sitch, now live in Chicago, still lead with your photos. Every frame is composed to crop cleanly to the vertical format the apps use.

How quickly will I get my photos?

Sneak peeks within 48 hours, and the full edited set the same week as your session.

What should I wear?

Outfits you'd wear on a good date: flattering, comfortable, and a little elevated. Solid colors and soft textures photograph beautifully. Bring a layer or two for variety. Before the session we'll go through what you're thinking.

Do you retouch?

Lightly. Color, light, and the small distractions get cleaned up. Skin keeps its texture and your face stays your face.

Can I use the photos anywhere?

Your images come with a personal license for dating apps and social media. Commercial use is a separate conversation.

What time of day is best?

The last two hours before sunset give the warmest, most flattering light, so most sessions are timed around it. Cafés and interiors work any time of day.

Can I book with a friend?

Yes. Roommates, siblings, and friends often book back-to-back sessions. Ask when you reach out.

Give them a reason to say hello

Tell me your date and the feel you're after. You'll hear back with availability, usually the same day.

Check your date(847) 212-8642
A young man in a gray jacket with a hood sitting on a concrete bench outdoors, making a triangle shape with his hands, with trees and a blurred urban background.
A young woman with long dark wavy hair and a friendly smile, wearing a black leather jacket, sitting outdoors near a red brick wall.
A smiling man with brown hair and a beard sitting on stairs, wearing a navy jacket, brown pants, brown gloves, and a blue checkered scarf.
A woman with dark brown hair wearing a black dress and a black leather jacket draped over her shoulder, standing in a modern kitchen.
A young man standing outdoors near water with a city skyline in the background, wearing a black jacket draped over shoulders, a light gray shirt, and black pants.
A woman with long dark hair wearing a black floral dress standing in front of a metal roller shutter, smiling at the camera.
Young man with short dark hair wearing a dark gray T-shirt with a white geometric logo and the word 'ELEMENT' on the front, standing in front of a beige wall with windows.
A woman with dark brown hair smiling outdoors on a balcony, wearing a navy blue dress and silver watch.
A smiling man sitting on outdoor steps, wearing a blue blazer, patterned scarf, tan pants, brown gloves, and hiking shoes.
A man wearing a blue coat and a blue plaid scarf standing in front of a colorful, geometric mural painted on a wooden wall.
A smiling young man with dark hair and a beard, wearing a tan hooded sweatshirt, a black puffer vest, and sunglasses hanging on his shirt, leaning against a white wall outdoors.
Smiling woman with shoulder-length brown hair wearing a white blazer, black top, and black pants, standing against a grey wall.
A smiling man with glasses wearing a blue shirt in a bright room.
A woman with long dark hair smiling and resting her chin on her hand, sitting outdoors.
A smiling man with glasses wearing a blue shirt, standing in a bright kitchen, arranging green succulent plants in a rectangular container on a white marble countertop.
A smiling man standing outdoors in a winter setting, wearing a dark blue coat, a plaid scarf, and a striped shirt, with parked cars and trees in the background.
A young man with short brown hair and a black t-shirt sitting in front of a wooden bookshelf filled with vinyl records.
A man with light skin, light brown hair, and a beard, sitting on stairs, wearing a dark blue coat, blue scarf, tan pants, and gloves, leaning against a white wall.
A man in a navy blazer, light blue shirt, and jeans leaning against a brick wall outside, smiling at the camera.
A woman stands outdoors against a plain wall, wearing a black top, black jeans, and a white blazer draped over her shoulders, with her hands in her pockets, smiling at the camera.
A young man wearing a black coat and holding sunglasses, leaning on a black railing outdoors during daytime.
Young woman smiling, wearing a denim jacket and black pants, outdoors in an urban setting with trees and buildings in the background.
A man wearing glasses and a blue t-shirt smiling while arranging succulent plants in a kitchen.
A man standing outdoors in a snowy landscape, wearing a dark coat and a beige scarf.
A smiling woman with dark brown hair in a blue shirt dress, standing outdoors beside a wooden wall.
A smiling man with short dark hair wearing a tan jacket, white t-shirt, black pants, and a necklace standing against a two-tone gray wall.
A young man with brown hair and blue eyes stands outdoors on a snowy day, wearing a dark navy winter coat with large buttons and a beige scarf around his neck, with a black metal fence and snow-covered grasses in the background.