We’ve all been there: you’ve met the object of your affection, whether you think it might just be a crush or something more serious, and now it’s time to make the first move. In the old days, you would just hop on the phone and ask the person out, but nowadays things are way more complicated. What with texting, Emoji, and the potential ramifications of everything from an exclamation point to the misuse of ‘LOL,’ there’s a lot that can go wrong.

Ruben and Sam are real-life, long-time best friends, roommates in Brooklyn, and collaborators on a number of sketch comedy projects. They’re always there for each other, but sometimes they don’t have the best advice. So what should Sam do when he gets a text from a girl he’s crushing on? Will he manage to ask her out? To get the confidence necessary to tackle that text, you need some good friends who have your back, and to tackle that first date, you need a killer smile, which you can get by brushing twice daily with the Philips Sonicare DiamondClean power toothbrush.

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This post is a sponsored collaboration between Philips Sonicare and Studio@Gawker.