For some of us Valentine's Day brings a lot of tough emotions to the surface and remind us of our own loneliness or shortcomings in love. Instead of thinking about your own heartbreak all day, let's remember the terrible heartbreak that some of our favorite fictional characters have gone through. After all, if they could get through their separations, believe you can too.

1. Lily and Marshall, "How I Met Your Mother"

Lily wanted to make her own mistakes and left Marshall to pursue art in San Francisco. Marshall was left heartbroken in the rain with her engagement ring. I cry every time.

2. Buffy and Angel, "Buffy the Vampire Slayer"

If David Boreanaz hadn't been so talented and gotten his own show, perhaps they wouldn't have broken up. But even though they loved one another they knew that as a vampire and a vampire slayer... they just really couldn't be together.

3. Cory and Topanga, "Boy Meets World"

They broke up over a lot of silly reasons, but still. Did Topanga ever really think they wouldn't end up together?!

4. Sam and Diane, "Cheers"

She tried to change him for the better, and in some ways she did, but these two were just never meant to work.

5. Bones and Booth, "Bones"

These two never actually broke up once they got together, but when Bones tells Booth she loves him when he's in love with another woman... LET ME DRY YOUR TEARS, GIRL. P.S. David Boreanaz stop breaking hearts.

6. Carrie and Sebastian, "The Carrie Diaries"

I know they broke up a record amount in only two seasons, but they had real chemistry. Then again who wouldn't have chemistry with Austin Butler.

7. Seth and Summer, "The O.C."

This relationship gave us all hope that we could possibly receive mutual affections of someone we've been lusting after forever. When it happened, it was a dream come true for all of us. Maybe they didn't have anything in common but what they did was IMPORTANT.

8. Meredith and Derek, "Grey's Anatomy"

Let's not even talk about Derek.

9. Luke and Lorelai, "Gilmore Girls"

He's the first person she ever really loved. They should be together. LUKE AND LORELAI FOREVER.

10. Brooke and Lucas, "One Tree Hill"

We all saw this coming, but it doesn't make it hurt any less. RIP to all the times Brooke called him "Boyfriend" and he called her "Pretty Girl." Thanks Peyton.

11. Jim and Pam, "The Office"

They never actually broke up when they were together, but before they were perfect Jim confessed his love to Pam and she didn't say it back. Jim transferred from Scranton and the months he was basically broken up with Pam were almost too much to take. It's a good thing Rashida Jones is beautiful.

12. Eric and Donna, "That 70's Show"

Sometimes I still don't understand how these two ever got together. However Eric and Donna had an innocent kind of love that was really about the other person and how they made each other feel. When they broke up--and when Eric left-- it was obvious they would never feel the same about anyone else.

13. Ross and Rachel, "Friends"

Every moment in their multiple hour-long break up felt like we all accidentally cheated on Rachel and just wished we could undo it. I cannot think of a more painful 22 minutes.

14. Stefan and Elena, "The Vampire Diaries"

He loved her more than he ever thought he could love someone. LOOK AT THE PAIN IN HIS FACE. THAT IS LOVE. Fake prophecy or not, Stelena were destined for one another. Their inability to stay apart proves that.

15. Belle and Rumple, "Once Upon a Time"

“You would never give up power for me, Rumple. You never have and you never will. I tried to be everything for you but I wasn’t and I lost my way trying to help you find yourself.”

Belle gave him so many chances and tried so hard to save him, but he could never fully give himself to her.

16. Lindsay and Nick, "Freaks and Geeks"

Parents should never ever get involved with the high school dating scene. Ever. We will never know how deeply Lindsay actually cared for Nick because her mother told him her daughter meant to break up with him. Who does that?!

17. Jane and Rafael, "Jane the Virgin"

They're an entirely unlikely couple but the way they grew together over the first season proves the connection they have. Sure Rafael should've just been honest with Jane instead of trying to "protect" her, but he did it out of love. Michael can leave.

18. Nick and Jess, "New Girl"

This has happened to a lot of us. Honestly, the saddest thing about this breakup is how obvious it is they care for one another, but they just weren't meant to be.

19. Sheldon and Amy, "Big Bang Theory"

Right when Sheldon was finally ready to commit to Amy, she ended things. It may have taken Sheldon years to get to this point, but you could tell that he really loved her.

20. Leslie and Ben, "Parks and Recreation"

Their amicable yet rough split was so heart wrenching because it was so obvious they belonged together. So instead to conclude, let's remember when they got back together and Ben proposed to Leslie and it was the most beautiful thing ever.