Meaning
To be romantically involved with someone — going with, seeing, or dating them. From 'deh' (to be / to be there) plus 'wid' (with): to 'deh wid' somebody is to be in a relationship, short of or on the way to living together. Milder and more everyday than announcing an engagement; it is how people describe who is courting whom.
Examples
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Dem deh wid each adda from schooldays.
They've been together since their school days.
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A who yuh deh wid now?
Who are you seeing now?
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Shi nah deh wid nobody right now.
She isn't with anyone right now.
Origin
How it’s used
To be dating/going with someone. A step short of Shack up (living together).