During the mid-1980's, a serious romantic relationship developed between Akina and her "Ai Tabidachi" co-star, Kondo Masahiko. At this time, Akina's career was soaring with success following success. Kondo's career, on the other hand, had declined significantly from his early 1980's high. Some of Kondo's critics would even speculate later that his relationship with Akina had been driven largely by the desire to maintain his career. The idea being that, simply by basking in Akina's popularity, he could continue to enjoy a measure of popularity himself.

Whatever the case, by late 1987, the relationship had become strained and by mid-1988 it had, for all intents and purposes, reached an end. In late 1988/early 1989, Akina began to show signs of fatigue and her diminishing weight became a cause for concern. Following the public disclosure of a scandalous tryst between Kondo and Matsuda Seiko, Akina attempted suicide on July 11, 1989 at Kondo's Roppongi appartment.

While the extent of her injuries was not severe, the resulting publicity tarnished her previously perfect public image and produced a decline in her popularity. Because it occurred at a time when Akina appeared to be at the height of her career, it was difficult for the public to understand the reasons behind what seemed to be an extremely ill-conceived gesture.

For a time, Akina virtually disappeared from public view as she struggled through a personal bout with depression. Then, at a December 1989 press conference, Akina cleared the air, publicly apologizing for her actions and explaining the circumstances that had led to her reaching such a point of desperation.

By 1990, Akina had withdrawn to Hawaii in an attempt to recover and forget this black year in her private life. Although Akina would make her return later the same year, her fans continued to worry. She smoked excessively and had started to drink quite heavily as well.

To the delight--and relief--of her fans, Akina released her 25th single on July 17, 1990. "Dear Friend" was a very cheerful song which contrasted sharply with her state of mind at the time. Another single, "Mizunisashita Hana," would follow in November of that year.

In 1991, Akina's 27th single "Futarishizuka" would mark the end of her collaboration with Warner-Pioneer Japan, which had been her recording company since her debut in 1982. In July of that year, Akina performed "Yume ~ '91 Special Live," two-dates of special concerts held at Makuhari Messe in Chiba. Evident during the performance was her fragile emotional state (she had just learned of Kondo Masahiko's marriage a day earlier) and poor physical condition. It appeared that Akina might never recover from the breakup with Kondo, for that relationship had consumed several years of her life.

Akina produced no original albums for a period of four years. Only some live album and best collection releases would serve to prevent her from fading from the public consciousness. This would be the longest period of relative inactivity of her career.

Akina busied herself with other work during this time. In 1992, she launched her very own radio show called "Fifty Off" which aired on Tokyo FM and ran for 90 weeks from April through December of 1993. Akina also appeared in a number of made-for-TV dramas, the best known of which was the very successful 1992 series "Sugao no Mamade" which co-starred Yasuda Narumi.