Theodore's first date is the 2nd episode of season 6.
Theodore wants to ask Emily to go out with him, but he's too scared that he'll make a mistake and get laughed at. But when Thomas tells him about his first time asking someone out, Theodore begins to feel better. He soon asks Emily if she'll go out with him and she says 'Yes'. Now Theodore doesn't feel silly.
- Thomas the Tank Engine
- The Dispatcher
- Benjamin Bridge (cameo)
- Owen (cameo)
- a green pilot boat that may be pearl (cameo)
- This is the first episode in which a Tugboat goes on a date with another Tugboat.
- Characters from Thomas and Friends are mentioned.
Narrator: It was a clear, sunny morning in the Big Harbor. All the tugs were hard at work. All of them, except for one. Theodore was given the day off. He couldn't stop thinking about Emily. He didn't know why, but somehow she made his life feel complete. Later Hank came by.
Hank: Morning Theodore.
Theodore: Hi Hank.
Hank: Wanna go watch some TV?
Theodore: No thanks.
Hank: So what's on your mind? Girls?
Theodore: SHUT UP HANK!
Hank: Let me guess. You can't stop thiking about Emily.
Theodore: How'd you know?
Hank: Lucky guess.
Theodore: Well, she's amazing, she's beautiful, and she's very smart. Whenevert I'm near her I feel different.
Hank: Well, that means only one thing. YOU'RE IN LOVE WITH HER!
Hank: Yep. You're in love with Emily.
Theodore: Wow. So that's what love feels like. What should I do?
Hank: Ask her out.
Theodore: But she's an Ocean Tug and I'm a Harbor Tug. We're star-crossed lovers!
Hank: Romeo and Juliet were star-crossed lovers, but that didn't stop them.
Theodore: Yeah. And they ended up dead.
Hank: What's your point?
Theodore: My point is, I'm too scared!
Hank: Just have faith.
Theodore: Why are you helping me?
Hank: Cause you're my friend.
Narrator: Just then George came by. He had overheard the whole thing.
George: SO you want to ask Emily out huh?
Theodore: Uh, yeah?
George: THAT'S WONDERFUL!
Theodore: It is?
George: No one else has asked her out. And I was hoping that guy would be you. Besides, YOIU'LL GET TO BE MY BROTHER-IN-LAW!
Theodore: Uh, your welcome?
Narrator: Later that day, Theodore was getting ready to ask Emily out.
Theodore: Here she comes.
Narrator: Emily was heading for the dock when she saw Theodore.
Emily: Oh, hi Theodore.
Theodore: *Tries to speak but nothing comes out.
Narrator: Theodore was so nervous. And he raced off without a word. Emily was puzzled.
Emily: Wonder what's the matter with Theodore.
Narrator: Theodore had hidden by some ships. He was so upset.
Theodore: I can't do it. I knew I couldn't be brave enough to ask her out. Now she thinks I'm wierd and she'll never want to see me again.
Voice: I wouldn't be so sure.
Narrator: Theodore turned around. It was Thomas the Tank Engine.
Thomas: Having troubles, are you?
Theodore: I just don't know what to do Thomas. I want to ask Emily out, but I'm too scared.
Thomas: Well Theodore, believe it or not, I was also scared to ask someone out.
Theodore: You did?
Thomas: Yep. Her name was also Emily. She was an Emerald Green Tender engine. She had great big wheels and was very beautiful. When I wanted to ask her out, I felt scared. I thought she would be interested in a big, strong engine like Gordon James or Henry and not a silly tank engine like me. But then my best friend Percy told me to have courage. And he told me to remember to myself "Today is the First day of the rest of your life."
Theodore: Then what happened?
Thomas: It worked. She said yes and we've been together ever since.
Theodore: So you're telling me that all I have to do is feel confident and she's want to be with me?
Thomas: That's right.
Theodore: Okay. I'll go do it.
Narrator: Theodore went back to find Emily.
Theodore: (To himself) Alright Theodore. Today is the first day of the rest of your life.
Narrator: Then he saw Emily again.
Theodore: (Gulp.) Uh, Emily, w-w-w-would you g-g-g-go out w-w-w-with me?
Emily: Theodore, are you asking me if I would be your girlfriend?
Theodore: Uh, yes. Yes I am.
Emily: I'd LOVE TOO!
Theodore: Phew! I did it! But I thought a beautiful Ocean Tug like you wouldn't want to go out with a silly Harbor Tug like me.
Emily: It doesn't matter what you are Theodore. All that matters is how nice and sweet you are to me.
Narrator: So, Thomas' advice had worked, Theodore and Emily became Boyfriend/Girlfriend, and Theodore is no longer nervous to be by her.