The devils in the details

You had a pretty average life, but you always wanted more, but you were too scared to do so. To shy to ask your love interest, to cautious to go after your dream job, and to anxious really live, But you got an offer that could change that a deal that could let you be who you've always wanted to be, but there's a catch. A mysterious man with unusual features offered to let you redo your life and try it differently. The catch you must complete three tasks before you reach the age you currently are. You must get one kiss from your love interest (willingly), hold your dream job for a year, and lastly, find contentment in your life. What happens if you don't? well, at the time, it seemed harmless he would take one day of your life. Of course, he failed to mention that the day he would take would be the day you were born. Now, you must complete the challenges ahead of you, or you will be completely erased from existence. Can you beat the trickster at his game and complete the challenge, or will you completely be erased. Notes: Hey, very big shout out to @LewdLeah for putting in the work to create the auto card script.