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The Boyhood Crush date idea illustration

The Boyhood Crush

Duration: variable

Revisit your childhood and relive your crush on your best friend's older sister Emma. From babysitting adventures to picnics and goodnight kisses, this roleplay takes you on a journey from innocence to adulthood. Will you finally get your chance with Emma?

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  • You're 10 years old again, and your best friend's older sister, the beautiful Emma, is babysitting you for the day. She's 16, and you can't help but have a crush on her. You're playing games, watching movies, and running around the house all day. As the day goes on, you start to notice the way she laughs, the way her hair falls, and the way she smiles at you.
  • As the afternoon sun begins to set, Emma suggests you have a picnic in the backyard. You're thrilled to be alone with her, and you can't help but steal glances at her as you eat sandwiches and drink lemonade. As you're cleaning up, Emma accidentally spills lemonade on her shirt, and you quickly offer to help her clean up. As you're washing the stain, your hands touch, and you feel a jolt of electricity.
  • As you're getting ready for bed, Emma tucks you in and gives you a goodnight kiss on the forehead. You can't sleep, thinking about the way her lips felt on your skin. You start to wonder what it would be like to kiss her on the lips.
  • Years go by, and you're now 18, and Emma is 24. You're home from college for the summer, and you run into Emma at the local park. She's even more beautiful than you remembered, and you can't believe your luck. You strike up a conversation, and before you know it, you're taking a walk together, reminiscing about old times.
  • As the walk comes to an end, Emma turns to you and asks if you want to grab coffee with her. You can't believe your luck. You're finally getting a chance to make your childhood crush a reality.

Preparation steps:

  • To set the scene, create a playroom or a designated area with toys, games, and kid-friendly snacks to transport you back to your childhood. You can even set up a picnic area in your backyard or living room to recreate the afternoon picnic.
  • Dress the part - wear clothes that remind you of your childhood, and have your partner dress up as the older sister or babysitter. You can even add props like toys, books, or stuffed animals to get into character.
  • To make the experience even more realistic, create a playlist of popular kids' songs or TV shows from your childhood to play in the background.

You may need

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Some tips:

  • To get into character, think back to your childhood crushes and what made them so special. Channel those feelings and emotions to make the roleplay more authentic.
  • Don't be afraid to get creative and add your own twists to the scenario. Maybe you want to recreate a specific memory or event from your childhood, or maybe you want to take the roleplay in a completely different direction.
  • Remember to communicate with your partner throughout the roleplay to make sure you're both comfortable and having fun. This is a chance to relive your childhood fantasies and explore new desires with your partner.

Dialogue ideas:

  • You know, Emma, I always felt like I was so lucky to have you as my babysitter. But now, I feel like I'm the luckiest guy alive to be spending time with you like this. You're still taking care of me, but in a much more adult way.
  • Emma, you're even more gorgeous now than I remembered. I have to admit, I had a huge crush on you when we were kids. I used to dream about you at night.
  • I've been thinking about that goodnight kiss you gave me all those years ago. I wish it had been on the lips. Do you think... maybe we could try that now?
  • Oh Emma, I think I got the stain out. Your shirt is spotless now, but I have to say, I'm a little sorry to see the stain go. It was a great excuse to touch you.
  • Emma, I've got to ask, did you ever think about me when we were apart? Did you ever wonder what would happen if we kissed? Because I've been wondering that for years.

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