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悔しいやししい~い Adj.Freq #1594
1

frustrated (over a failure, humiliation or injustice); annoyed; chagrined; (bitterly) disappointed; bitter; vexed; frustrating; annoying; regrettable

Examples
監督はチームをトーナメント優勝に今一歩という所までもっていったのに悔しいことだった。
It was annoying, as the manager took his team to a near-miss in the tournament.
しい~い Adj.Freq #2679
1

regrettable; disappointing; unfortunate

Examples
あなたほどの才能の持ち主が世間に知られずにいるのは惜しいことです。
It is a pity that a man of your ability should remain unknown to the world.
2

precious; dear; valuable

Examples
命は誰でも惜しい
Life is dear to everybody.
3

too good for; deserving better

Examples
これはまだ捨てるには惜しい
This is still too good to be thrown away.
4

almost (but not quite); close (but no cigar)

名残しい名残りしいごりおし~い Adj.Freq #9192
1

reluctant (to part)

負けしみけおしみNounFreq #19009
1

being a poor loser; unwillingness to admit defeat; sour grapes

Examples
日本の市場が閉鎖的だという非難は、負け惜しみにすぎません。
Criticisms that Japan's market is closed are just sour grapes.
しみないしみ無いおしみない~い Adj.Freq #19011
1

generous; unstinting

しげもなくし気もなくしげも無くし気も無くおしげもなく気もなくAdverbExpressionFreq #22010
1

freely; generously; liberally; ungrudgingly; unsparingly

Examples
彼はいつも惜しげもなく金を使う。
He always spends his money freely.
出ししみしおしみNoun~する VerbFreq #22809
1

being reluctant to give out (pay, provide, etc.); giving out grudgingly

たらったらAdverbUsually kanaFreq #31304
1

alas; regrettably; to my great regret; tragically

いせきいじゃくNounTransitive~する VerbFreq #66253
1

missing someone; loathing to part

いせきNounTransitive~する VerbFreq #69445
1

grief; sorrow

きべつNounFreq #71877
1

reluctance to part; sorrow at parting

きはいNounIntransitive~する VerbFreq #93367
1

regrettable defeat; defeat by a narrow margin

しげし気しげNounFreq #114126
1

reluctance; regret; frugality

きしゅんNounFreq #138376
1

lamenting the passing of spring; lamenting the passing of one's youth

うせきNounTransitive~する VerbFreq #165898
1

deep regret

敗率せきはいりつNounFreq #295505
1

ratio of the margin of loss of an electoral candidate in a single-constituent district (used to break ties when determining the representative of a proportionally represented district)

別れをしむわかれをおしむExpressionGodan verbFreq #27944
1

to loathe to part (with); to be reluctant to leave (someone)

しむらくはむらくはExpressionFreq #45175
1

it is to be regretted that ...; it is a pity that ...; it is unfortunate that ...

寝る間もしんでねるまもおしんでAdverbExpressionFreq #45870
1

without sparing time for sleep

命をしむいのちをおしむExpressionGodan verbFreq #47317
1

to hold one's life dear; to be reluctant to die

命がしければいのちがおしければExpressionFreq #51473
1

if you value your life

出ししむしおしTransitiveGodan verbFreq #55269
1

to grudge; to begrudge; to be stingy; to be unwilling to pay

時間をしむじかんをおしむExpressionGodan verbFreq #59352
1

to value time

Examples
彼は自分の研究に時間を惜しまなかった
He didn't spare time on his studies.
しげなくし気なくしげ無くし気無くおしげなくAdverbFreq #81143
1

freely; generously; liberally; ungrudgingly; unsparingly