Ashley Benson news, gossip, photos of Ashley Benson, biography, Ashley Benson boyfriend list Relationship history. Ashley Benson relationship list. Ashley Benson's dating timeline, pictures of boyfriend history, photos in by: Alexandra Daluisio on June 8, at pm EDT | in Celebrities | 0 Comments. MailOnline US - news, sport, celebrity, science and health stories . Hailey Baldwin and co-stars Shay Mitchell and Tyler Blackburn joined Ashley for the Model sandwich: The birthday girl posed for a funny photo between her two friends. It's rumored that Ashley and co-star Tyler Blackburn are dating. 7 Facts About Riverdale's Sexy Outcast, Cole Sprouse 19 Times Ashley Benson and Tyler Blackburn Proved They Were Perfect For Each Other The duo may be one of the cutest onscreen couples, but does their relationship go beyond the TV drama? There are Celebrity and Entertainment Newsletter. Tyler Blackburn Took On-Screen Dating History With Ashley Benson To The Next Level; Co-Star Turned Into Girlfriend? Moreover, Tyler posted a romantic image with Ashley on her birthday expressing his love of past five years and gratitude, that created a hype .. Want to more about your celebrities?. Date night: Ashley Benson and her beau Ryan Good were seen leaving The Ryan coordinated with his girlfriend, wearing a black T-shirt and.