なぜかうまくいかず、目下全戦全敗、「彼女いない歴＝自分の年齢」という寂しい生活を送っていました。

Sentence Analyzer

English Translation

For some reason it didn't go well, shot down at every attempt, and he led a sad "History of no girlfriend = Age" life.

Furigana

なぜかうまくいかず、目下(もっか)全戦(ぜんせん)全敗(ぜんぱい)、「彼女(かのじょ)いない歴(れき)＝自分(じぶん)の年齢(ねんれい)」という寂(さび)しい生活(せいかつ)を送(おく)っていました。

Romanji

Naze ka umaku ikazu, mokka zensen zenpai," kanojo inai reki jibun no nenrei" toiu sabishii seikatsu o okutteimashita.

Words

何故 (なぜ、なにゆえ)

why; how

か (か)

indicates a question (sometimes rhetorical); or; whether or not; some- (e.g. something, someone); indicates doubt, uncertainty, etc.; emphatic prefix; suffix forming adjectives or adverbs; in that way

上手い (うまい)

skillful; skilful; clever; expert; wise; successful; delicious; appetizing; appetising; tasty; fortunate; splendid; promising

行く (いく、ゆく)

to go; to move (in a direction or towards a specific location); to head (towards); to be transported (towards); to reach; to proceed; to take place; to pass through; to come and go; to walk; to die; to pass away; to do (in a specific way); to stream; to flow; to continue; to have an orgasm; to come; to cum; to trip; to get high; to have a drug-induced hallucination

目下 (もっか)

at present; now

全敗 (ぜんぱい)

complete defeat; losing all of one's matches; finishing the tournament with no wins

彼女 (かのじょ)

she; her; her; girlfriend; sweetheart

要る (いる)

to need; to want

歴 (れき)

history of; experience of

自分 (じぶん)

myself; yourself; oneself; himself; herself; I; me; you

の (の)

indicates possessive; nominalizes verbs and adjectives; substitutes for "ga" in subordinate phrases; (at sentence-end, falling tone) indicates a confident conclusion; (at sentence-end) indicates emotional emphasis; (at sentence-end, rising tone) indicates question

年齢 (ねんれい)

age; years

と言う (という、とゆう)

called; named; as many as; as much as; all X; every X

寂しい (さびしい、さみしい)

lonely; lonesome; solitary; desolate

生活 (せいかつ)

living; life (one's daily existence); livelihood

を (を)

indicates direct object of action; indicates subject of causative expression; indicates an area traversed; indicates time (period) over which action takes place; indicates point of departure or separation of action; indicates object of desire, like, hate, etc.

送る (おくる)

to send (a thing); to dispatch; to despatch; to transmit; to take or escort (a person somewhere); to see off (a person); to bid farewell (to the departed); to bury; to spend (time); to live one's life; to pass (down the line); to affix okurigana