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Struggling at the end...

Don bumped into another chap - and another
?A?D?E?H

Collector of rubbish maybe from road going north over border
D?E???

Fifth letter of the above clue is the first letter of...

Awkward person shows sentimentality when meeting female
??O?

dredge (RD road backwards + edge)

Collector of rubbish maybe from road going north over border .. DREDGE ('rd' backwards + 'edge').

Awkward person shows sentimentality when meeting female ... GOOF ('goo' + 'f').

JimC

Thanks to you both. I had dredge in mind, but the explanation makes it obvious.

The last one has me completely stumped though...

Don bumped into another chap - and another ... RANDOLPH (anagram of 'don' inside 'ralph').

JimC

Many thanks Jim. That one would have stumped me all week it's fair to say.