In high school, it can be intimidating for a teen boy to ask a girl he likes out, especially if he doesn't know if she has feelings for him. If your teen son is facing this situation, explain that if he doesn't do anything, she'll never know how he feels, or she might start dating someone else. Help your teen stand out from the crowd by coming up with creative and heartfelt ways to ask the girl out, flattering and impressing her so that it's almost a sure thing that she'll agree to date him.
Write it Out
Your teen can make a big impression by posting a large sign on his crush's school locker, asking her to go out with him. If he's artistic or has a friend that is, he can draw something sweet on the poster, like flowers or two people holding hands. He could also write out reasons he likes her on sticky notes and put them in a shape of a heart on her locker. Another idea is put a giant sign on her garage door at her home. If your teen son is friendly with her parents, he might also be able to put a sign or the sticky notes on her bedroom door.
Have your son keep his crush guessing who is trying to ask her out. He can easily make his own puzzle by writing "Will you go out with me?" on a piece of cardboard, then cutting it up into puzzle pieces. It doesn't have to be perfect. She will see the message as soon as she puts it together. Be sure he includes his name in the puzzle. Your teen can also send her on a scavenger hunt. Have him leave a clue in her locker that leads to another location to find the next clue. Clues could even be friends who hand her a clue to the next person. Each clue should include something related to your teen son's identity. The last clue will lead her to your son, where he can ask her out in person.
If your teen knows his crush has a sweet tooth, he can send her a baked goodie or candy treat to ask her out. For example, he could also send her a giant cookie with icing that spells out, "Go out with me?" or something similar. He could also have the local pizza joint spell it out on a giant pizza with pepperoni or another topping, and have them deliver it to his crush's house. Or, he could pick up some fortune cookies from a Chinese restaurant and carefully remove the fortunes without breaking the cookies. A paper clip might help. He can then replace the fortunes with his own notes, asking his crush out and predicting an amazing date.
Have your teen put his technology skills to good use and create a picture montage of moments he and his crush already shared. This is ideal if the two are already friends. He can set the montage to music and include a graphic that asks her out at the end. If your son can sing and play an instrument, record him performing a special song for his. Another idea is to have him send his crush a video with all their mutual friends telling her how much he likes her and why she should go out with him. Encourage him to be bold and post it on her social media page to show her that he is serious and not afraid to put himself out there for her.