Over the weekend, the 41-year-old actor was seen walking the streets in New York as he made his way to a nearby restaurant for a little one-on-one with a stunning brunette.
The Nightcrawler star was seen wearing a trendy oversized black The North Face jacket that he paired with a matching beanie and a comfortable pair of khakis.
The actor finished off his look with a sturdy white N-95 mask covering the majority of his face. Once Gyllenhaal made his way to the lunch table he decided to keep his face covering on for the entirety of the meal.
His mystery woman didn't seem to mind the mask and was seen laughing it up during the date. In snaps, Gyllenhaal's date was seen staring into the actor's eyes with a romantic gaze.
The actor's last girlfriend was Jeanne Cadieu. The two started dating in December 2018 despite a 15-year age difference. The woman in the photos does not appear to be Jeanne despite looking a bit similar. Gyllenhaal and Cadieu have not been seen together in some time.
The actor doesn't appear to be having any trouble finding lady friends despite Swift calling him out as a bad boyfriend in the new music video for her rereleased song All Too Well. She never specifically mentions Gyllenhaal but fans have put the clues together.
The 10-minute track talks about the 3-month relationship they had back in 2010. Swift didn't hold back accusing the actor of playing games with her heart and even failing to return her sweater — she believed he kept it to remember her by.
"And there we are again ... When nobody had to know ... You kept me like a secret ... But I kept you like an oath ... Sacred prayer and we'd swear to remember it all too well," she sings.
Gyllenhaal didn't respond to the song when it was first released in 2012 and kept his mouth shut when it was re-released in October.