Vocaloid/Heartwarming

"Angel Voice."
"I Like You, I Love You" Your mileage may vary...
Gemini. Just... Awww!
RinRin HIGH* MIND, a song about Rin being in love with her childhood friend and expressing her feelings.
Innocence is Miku asking for everyone to try to get along without dragging real-world problems into the fun parts of Vocaloid, as well as an expression of gratitude for all the songs that people have made for her. It was written in the midst of a bitter three-way copyright dispute that was threatening to break the fandom apart. In other words, the writer was trying to stop a Flame War by reminding everyone about why they loved Vocaloid in the first place. D'awww.
The end of Rolling Girl by Hatsune Miku, which was about a girl who was implied to be bullied and her world was spinning wildly out of her control. In the fanmade PV, when she was about to end it, the boy who was with the whole time reached out and held her, telling her it was going to be okay now.
Regret Message, the third of the 'Of Evil' series, as well as Daughter of White, which is Regret Message from Yowane Haku's point of view.
- Adding to this, there's Mothy's South North Story. Mind Screw aside, it's rather sweet when you consider the implications that the normal Rin has met the Rin from Story of Evil and appears to be trying to comfort her. D'awww.
- Kept Waiting for a Response, the finale to Story of Evil. And a touchingly beautiful finale it is.

If my wish really does come true
If my sins have really been forgiven
I want the response to my letter
And will keep waiting for it

Deco*27 never ceases to amaze his fans, and his new song, Once Upon A Me gives a nostalgic feeling that's sure to bring out the happy!waterworks.
"Smiling." Inspired by Nico Nico Chorus', and listening all the Japanese Vocaloids (with the exception of Piko, Gachpoid, and Iroha) singing this beautiful song gives such a heartwarming moment. then the best part of this video is when Len Raps.
"You're not alone".
'Reflect' is a song about a boy who doesn't believe he deserves others' attention. Is also a Tear Jerker.
In scissorsloid, Luka (at 3 minutes) is happy to see her "big sister Miku" visiting her room, and asks what she'll learn from her. She then proceeds to issue compliments that are very sweet, and she seems to really love and admire Miku, and it's an extremely heartwarming moment, especially because of the video's yandereness. That is, until she takes a knife and stabs her.
Reflection is absolutely sweet and it brings out those tears of happiness with just a bit of the bitterness.
"Cat Ears Switch", by Rin and Len. The little chiptune-y beat alone can give you the warm fuzzies.
"30 Seconds Love Story of a Little Demo "^{[dead link]} is an incredibly touching video featuring Miriam and Meiko.
Last Night Good Night is a heartwarming, happy-tear-jerking song about that feeling you get when you first feel love for someone, with an amazing video.
This rather suggestive video (NSFW) of Haku Yowane waking up in the morning following a night of passionate sex is one of very few moments of Haku experiencing genunine happiness. YMMV that it could imply being a Tear Jerker as well as some allege it's the kind of moment that happens before someone is going to die.
"Your Star" by Hatsune Miku. The sheer beauty and sadness of the song is what makes it so special.
GUMI's "Time-Warped After Chopping My Stag Beetle" is very weird at the beginning, exactly as the title sounds. However, at around three minutes, it takes a serious but uplifting turn. Gumi meets her future dying self, who tells her to live without regrets because she (in the future) doesn't want to be sad. Brings a smile to this troper's face each time.
"Let's Kiss, Hiding In A Car", a beautifully melancholy song by Kaito. Might also double as a Tear Jerker.
YMMV, but This Troper found this video, where Rin says she'll take the blame for Len's crimes, to be incredibly sweet.
This relatively unknown little song called "Grave Visiting" (hakamairi) definately counts for This Troper. It is about a little girl (Miku) who doesn't really understand why her parents visit the cemetary every summer with her. She keeps being bored and wants to go back home. Over the years she finally understands the meaning of those visits. In the second part of the song she is now an adult and still visits the cemetary every summer. She tells her grandfather how she fell in love with someone and got married and introduces her own child to her grandmother. This song also doubles as a Tear Jerker for this Troper at least.
Luka's The Lonely Princess and Attendant as well as The Lonely Youth
You people call yourself Vocaloid fans and yet you forget "Melt"?
KOKORO is a combination of Tear Jerker and Heartwarming Moment. The fact that Len spent his life making a program that would allow Rin to able to feel human emotions is already sweet. The song that Rin sings for Len, thanking him for all he's done, is what really pushes things into Tear Jerker and Heartwarming territory, especially when that song was able to reach Len.
Miku's "1/6", in which she plays a girl with aspirations to become an astronaut and go up into space in a satellite. However, he decides to postpone those plans and give up the money she was saving up for them after she finds out that her boyfriend has been going through some major depression. She takes him to a pier where they go up a lighthouse, insisting that he needs to be "elevated" to cheer up. This works and he slowly begins to smile. All throughout the song she promises him that when she gets enough money she will take him to the satellite with her, where all of his sadness will melt away and only be 1/6 of his weight. Awww!
This video, whose backstory is a fan's interpretation how Kaito became an Ensemble Darkhorse after the introduction of Miku.

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