Awkward person regularly in tears on date (4)
I believe the answer is:
nerd
'awkward person' is the definition.
(nerd can mean a socially awkward person)
'regularly in tears on date' is the wordplay.
'regularly' means one should take alternating letters (regularly take one letter, leave next etc.).
'on' means one lot of letters go next to another.
'date' becomes 'd' (common abbreviation eg in DOB, date of birth).
'in'+'tears'='intears'
The alternate letters of 'intears' are 'ner'.
'ner'+'d'='NERD'
(Other definitions for nerd that I've seen before include "Someone boring (about computers?)" , "Computer geek?" , "Geek, anorak (sl.)" , "Foolish or annoying person" , "Socially inept but knowledgeable person" .)