#42: Messenger Own
Every smooth pickup line starts with something akin to “You have the most beautiful eyes.” However, not everyone responds well to that line. Take this person and their crush, for example. After telling them they have the most beautiful eyes, they simply reply with “Thank you.” It gets worse from there.

The original texter continues to flirtatious chat with “What are you up to, cutie?” Of course, homeboy thinks this person’s talking about him when they say, “Talkin’ to this really cool dude.” This bro plays coy – “Really? Would I know him?” Cue all the winky faces. Unfortunately, they’re going on a date with this “cool dude.” Ouch.