OWASSO, Oklahoma - Police said the Owasso teens involved in a deadly crash had several run-ins with officers in the days leading up to it. Jacob Frogge was killed and Collin Lovelace badly injured in an early morning crash near McLean, Texas Monday, May 6.

Lovelace was driving the wrong way on Interstate 40 when he struck a vehicle head-on, killing a 33-year-old Arkansas woman and injuring a 2-year-old boy in her car, according to the Texas Department of Public Safety. Frogge was a passenger in Lovelace's vehicle.

Tulsa Police said they were investigating the two 18-year-olds in connection to a Tulsa hit-and-run wreck that took place on May 4 and for reportedly pointing a handgun at a woman and some children in the parking lot of an apartment complex May 5. 

The woman told officers at that time that Lovelace and Frogge were in a car parked in a handicapped parking space at the Three Lakes Apartments, Lt. Nick Boatman said in a news release.

One of the children commented on where they were parked, and one of the men apparently became upset and pointed the gun at the kids, the release states. 

"Officers attempted to make contact with the suspects at their last known address without success," Boatman said. 

Lovelace and Frogge also may have been with another Owasso teen who was arrested at Trail Days May 4 on weapons and public intoxication charges, police said. 

TPD said their information will be sent to the Tulsa County District Attorney's Office to determine if charges will be made against Lovelace in the incident at the apartment complex. 

Lori Fullbright will have more on this story in tonight's newscasts.