50 Singles On The Most Heartbreaking Reason They’ve Been Rejected

45. When I was fourteen my best friend wrote me a two page ‘break up’ letter. In the letter she explained that she needed to “improve her social standing” and that she couldn’t do that and still be associated with me. She outlined her fourteen step plan to become popular and apparently step three was to cut ties with all her unpopular or weird friends.

I only read a few lines before I gave it back and told her she was a moron, that it was a stupid plan and that she could do all that and still be unpopular. She just smiled sadly and wished me well in life, unfriended me from everything and refused to even look at me for two months.

Well eventually she realized her plan was bullshit and that her relationship with the ‘popular kids’ actually got worse because of it (sort of like the end half of Mean Girls) and came crawling back. I like to think I handled that whole situation with maturity and grace but it really messed me up for a while and it’s still one of the most hurtful things a person has ever done to me.

46. He told me it was weird dating someone so much younger, especially since I was just one year older than his little brother. This was lame, because he was only two years older than me – we were in high school. It was also a lie, because he later dated my best friend who was – admittedly – older than me. But only by ten hours and two minutes; we had the same exact birthday.