Bruno Kirby was 38 in When Harry Met Sally... when he played the character 'Jess'.
That was over 35 years ago in 1989.
In 2006 he died aged just 57, starring in 41 films in his career, 19 of those after When Harry Met Sally... was first released. If he were alive today he would be 75.
In When Harry Met Sally..., I think Bruno Kirby looks: