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Dariana
What does "with a long start on someone" mean? The context: "Tom was drinking happily with a long start on me "
Aug 8, 2016 5:32 PM
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this would be equivalent to: "he started way before I did".

long start on me = a head start on me.  

a metaphor would be: think about a race track.  If you were at the normal starting line, but your competitor got to start half way around the track, he/she would have "long start ahead of you". 



August 8, 2016
To add to Jeff, we can expect that the friends had met with the intention of drinking together for a long time, perhaps a whole evening. There is a sense of competition though we can imagine it is not a serious one.
August 8, 2016
Dariana
Language Skills
Chinese (Mandarin), English, French, Russian
Learning Language
Chinese (Mandarin), English, French