Date with title holder is a depressing experience (6)
I believe the answer is:
downer
'a depressing experience' is the definition.
(I've seen this before)
'date with title holder' is the wordplay.
'date' becomes 'd' (common abbreviation eg in DOB, date of birth).
'with' says to put letters next to each other.
'title holder' becomes 'owner' (I've seen this before).
'd'+'owner'='DOWNER'
'is' acts as a link.
(Other definitions for downer that I've seen before include "In slang, a depressant drug" , "Sedative" , "A sad thing" , "Informally a depressant drug" , "tranquilliser" .)