wistful

1. full of yearning or desire tinged with melancholy; also : inspiring such yearning
2. musingly sad : pensive

1. showing or evoking a sad longing for an often idealized past

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Urban Dictionary is community-written and may contain offensive or explicit language.

1. A [regretful] [longing]
2. A longing look into the distance, the [key] is to make it look like you naturally looking out at your loved one leaving for war, or in deep thought with a [touch] of [happiness] and a touch of sorrow.
3. An insincere, [sad] [attempt] at [smiling]
4. That point along the road to inebriated where you start to think about things that bum you out, [people] you [miss], and how you [wish] the situation you were drinking in was more enjoyable.

1. contemplative
2. pensive
3. melancholy
4. somber
5. mourning
6. depressed
7. cheerless
8. reflective
9. gloom
10. dismal
11. sadness
12. despondent
13. thoughtful
14. despair
15. sorrow
16. nostalgia
17. sadden
18. gloomy
19. elegiac
20. depression