RedEye Dating Campaign

Introducing RedEye Dating

RedEye is a news source and lifestyle brand for Chicago's urban young adults. RedEye partnered with How About We to launch a dating site for gay, straight, lesbian, bi, and curious singles in Chicago. RedEye Dating isn't about picking profiles. Participants describe their perfect evening, and a date decides to join them. RedEye needed an ad campaign that was fun, inclusive, and nothing like the usual cheesy dating ads.

My Role

Art Direction




Art Production


Jessica Schuh: Brand Manager, Copywriter

Ken Lyght: Creative Director

RedEye Dating illustration base color by Katie Wasserman
RedEye Dating llustration brush detail by Katie Wasserman
RedEye Dating llustration shading and brush detail by Katie Wasserman
RedEye Dating straight couple playing video games by Katie Wasserman
RedEye Dating lesbian couple with pizza by Katie Wasserman
RedEye Dating gay couple with drinks by Katie Wasserman

The Design Process

I brainstormed concepts with Jessica. She shouted out possible headlines while I scribbled possible artwork on post-it notes. We agreed on three couples: gay, lesbian, and straight. The couples would be doing fun and casual date activities like dinner, drinks, and old-school video games.

I drew the illustrations in Illustrator, starting with the base color layer and adding contours over the base. I added additional detail and shading with the brush tool. I didn't blend the contours on purpose. It keeps the contrast dramatic like candle light after dark. I kept the background red for the extra warmth, and it also happens to be RedEye's identifying color.

The people in the illustrations are very loosely based on people I've known that would look visually interesting paired together. The gay couple's drinks are real drinks that I would like to mix up someday: a kiwi champagne cocktail and a raspberry cosmo.

When the illustrations were done, I designed the full-page ads. I used RedEye's editorial type family for the headline and added a fat outline for extra sass. I resized the full page ads into half-page and quarter-page print ads. I created animated digital ads in cube, leaderboard, and mobile sizes. I did all of the art production for print and digital.

Successes and Achievements

The positive response from Chicagoans was huge. One RedEye reader liked the gay couple so much he took a photo of the print ad in the paper, posted it on instagram and tweeted "Nailed It." It was re-tweeted by Chicagoans of all sexual orientations. One of the WGN news anchors pinned the print ad on his wall of art, and it got air time on WGN Morning News.This is what advertising is really supposed to do: generate its own publicity and goodwill for the brand.

Lessons Learned

The more detailed the illustration, the more time it takes to finish. To get client buy-in earlier, I made a low-fidelity proof-of-concept with just the base color. This turned out to be a good plan. The client got on-board early and was excited about, not surprised by, the finished ad.

I had never done this style of illustration with contours and brush detail before, so of course it took longer than I thought it would take. I put in some nights and weekends to get these ads out the door. Next time I will plan more time.

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