50 Boys On The Dumbest Thing They’ve Ever Done For A Pretty Girl 

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23. I made a mix tape of me singing 90’s cheesy love songs.

24. Into this hippie chick I college. The moment I found out her and her bf were having issues I spent over $200 (basically everything I had as a broke college kid) on tie dye clothes and grateful dead apparel.

End of the day, we ended up dating for about 1.5 years.

25. I bought a girl an iPod Touch to try to get her to like me. Its one of the cringiest things I ever did in my life.