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‘Shoot Your Shot J’: Jaden Smith Seemingly Flirts with Chloe Bailey Underneath Her Comments Section, Leaving Fans Shook

Jaden Smiths subtle compliment under Chloe Bailey‘s Instagram photo on Thursday, April 29, caught fans’ attention after it appeared the rapper was “shooting his shot.” In the particular post, Bailey, who was seen wearing a skin-tight, short leather dress with black pumps, captioned the image: “she’s dangerous.”

Smith replied to the upload by writing, “She really is.” Although it is unclear what the “Icon” lyricist meant by that statement, this interaction between the two artists is one of three within the past couple of weeks. On April 19, Bailey commented one fire emoji under a post by Smith with the caption, “I’m Tryna Deluxe Myself.” A week prior, Smith reposted a tweet of the songstress on a spin bike that read, “Remember when Chloe Bailey….”

Jaden Smith seemingly shoots his shot under a recent photo of Chloe Bailey, leaving many speechless. Photo:@chloebailey @c.syresmith/Instagram

In the past, Smith has reportedly dated Kylie Jenner, actresses Amandla Stenberg, Madison Pettis and Stella Hudgens. His most recent alleged romance was with actress Cara Delevingne. The alleged couple was spotted kissing earlier this year after he gave her a bouquet of flowers. The pair met on the set of their film called “Life in a Year,” a movie about a teenage boy trying to give his terminally ill girlfriend, who has a year to live, a lifetime full of experiences. 

Bailey has been linked to her “Grownish” co-star Diggy Simmons in the past, but the “Do It” singer confirmed she was single during a 2020 interview with “The Breakfast Club.”  

Although it is not confirmed that anything is going on between Smith and Bailey, many couldn’t help but express their initial reaction to Smith’s response. Some were speechless over the gesture, while others encouraged “The Karate Kid” star to make his move.

“Not u in the comments.”

“Hold on now💃🏾.”


“Shoot ya shot J.”

“I would like to see this.”

“Get em J. Go big or go home.”

Bailey isn’t a stranger to making headlines when it comes to her social media page. Fans and blogs have observed the “Do It” vocalist upload provocative posts and respond to trolls who take issue with what she puts on her page. Last month, Bailey shared a tip on how she deals with the haters by tweeting one’s validation and worth comes from themselves, and the moment they realize it, the more powerful that individual becomes.

She said, “Any time you see someone say a negative comment about you that bothers you, click on their page x I promise you’ll feel a whole lot better. somehow it takes the power of the statement away x reminds you that the only thing that truly matters is how YOU see yourself. ”

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