Toronto police say the victim was shot while sitting in the passenger seat of a car parked behind an apartment complex at 44 Willowridge Rd., near Eglinton Avenue West and Martin Grove Road.
"Due to his condition, members of the homicide squad have been notified, and we are currently assisting 23 Division in this investigation," Det. Ted Lioumanis told CBC News.
Police were called to the scene shortly before 1 a.m. on Tuesday.
They say the victim, who lives in the neighbourhood, was discussing engagement plans with his fiancee when the shooting occurred.
"While in their car having a conversation, the suspect approached and at this point fired shots, striking the victim," said Lioumanis.
A police report said the victim was shot through the closed front passenger window. The man was rushed to hospital with life-threatening injuries.
Police say they do not have any knowledge of an altercation taking place prior to the shooting, and the victim was not previously known to police.
Lioumanis said the victim is a "very well-respected person" in the local community.
The suspect is described as male, brown, wearing a light-grey hoodie and a white/black bandana covering his face. He was seen fleeing southwest of the area after the shooting.
Police are appealing to any witnesses, especially those living in and around the Willowridge complex, for any information. They are also asking anyone who may have had contact with the victim earlier that day to contact investigators.
Anyone with information is asked to contact Det. Sergeant Joel Kulmatycki or Det. Ted Lioumanis at 416-808-7400 or call Crime Stoppers anonymously at 416-222-TIPS (8477). People can also go online at www.222tips.com or text TOR and a message to CRIMES (274637).