Chicago

Woodlawn Love Trap: Dating App Meetups On South Side Block End In Gunpoint Robberies

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Published on February 16, 2026
Woodlawn Love Trap: Dating App Meetups On South Side Block End In Gunpoint RobberiesSource: Unsplash/Michael Förtsch

What was supposed to be a romantic meetup turned into a nightmare on the South Side, as Chicago police issued a community alert Sunday after two robberies on the same Woodlawn block tied to a dating app connection. In both cases, people who had matched with a man through a dating app were held at gunpoint in the 6600 block of South Woodlawn Avenue.

According to police, the incidents happened just a week apart: one in the early hours of Thursday, Feb. 5, and the other in the late-night hours of Thursday, Feb. 12. In each robbery, victims complied with the suspect's demands. As of Sunday, no arrests had been reported.

Police Release Suspect Description and Timeline

Chicago police described the suspect as a white or Hispanic man about 22 years old, between 5-foot-8 and 6-feet tall and weighing roughly 150 to 190 pounds, wearing a black jacket and black pants, according to CBS Chicago. In both encounters, officers say the robber produced a handgun, demanded property, then took off from the scene.

Detectives are asking anyone who may recognize the description or who was in the area around those dates to contact Wentworth-area detectives at 312-747-8380 or submit an anonymous online tip using reference number P26-1-017.

How To Submit Tips

Police are urging anyone with information, no matter how minor it might seem, to submit an anonymous tip through CPDTIP.com, referencing case number P26-1-017. They are also asking neighbors to hang onto any surveillance or doorbell-camera footage from the 6600 block that might show the suspect or his direction of travel.

Investigators say even small details can help move the case forward: a vehicle make or color, the way the suspect walked, or a remembered social media handle could help link these incidents to other reports.

A Troubling Pattern In Woodlawn

The two recent robberies echo warnings issued late last year after multiple women reported being lured via dating apps and then assaulted or robbed in Woodlawn, police told reporters. Reporting by the Chicago Sun-Times described several cases in October and December in which a man led victims into apartments, showed a gun and stole their property.

Community advocates and officers say the pattern highlights the risk when app-based meetups move from public spaces into private residences. Safety advocates recommend meeting in public, letting a friend or family member know where you will be, and keeping your phone charged with location services enabled. Police stressed that past cases in the area have been solved with help from community tips and video, and urged anyone with possible information to come forward.