First, Tyga was trying to convince his girlfriend Kylie Jenner to marry him without a prenup, and now the 25-year-old rapper reached out to Caitlyn Jenner and asked for her permission to marry her youngest daughter.

Tyga has been reportedly waiting for his teen girlfriend to turn 18 so he could propose to her and he is trying to win Caitlyn over with his suave antics.

“When Tyga realized he knew he wasn’t going to be able to attend [the ESPYS], he sent Cailtyn up a dozen of white roses with a bottle of Ace of Spades champagne. His letter was overboard though," an insider tells HollywoodLife exclusively.

"Tyga got a bit bold and wrote this sweet little note about how much he loves Kylie, and asked Cailtyn if she has the courage to give her permission for him to marry Kylie," the insider added. The rapper also wonders if Caitlyn could "do the honor of walking her daughter down the aisle.”

Tyga and Kylie, who have been going strong despite the recent cheating scandals, are not on the same side of the pre-nup issue. While Tyga does not want a pre-nup, Kylie has reportedly promised her family that she would not get married without protecting her money.

"If and when they do get married, Kylie will have a pre-nup in place and it will be air tight like a coffin," said one source. "She’s promised her mother, her father and her sisters that she will protect her money and the empire the family has created if she were to get married.”

The news reportedly forced Caitlyn Jenner to warn Tyga that she does not want her daughter to move in with him now. “Caitlyn listened and addressed some her of her concerns, like the age difference, and told Tyga it’s too soon for him to be living at her daughter’s house,” another source said.

But Tyga is not backing down and that's why he slipped that letter along his gifts for the prestigious Arthur Ashe Award winner.

“Tyga’s really on a mission to win Cailtyn’s trust. He doesn’t want Cait to think he’s an opportunist or to look at him sideways," the insider continues. "He wants her to accept him the way she accepts Kanye [West]."

Caitlyn reportedly smiled and laughed when she read Tyga's letter and she said "this man is something else, he’s a charmer all right."

It is unsure if Caitlyn took Tyga seriously or she's sticking by her words that the couple are moving way too fast in tying the knot.