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I am writing some sentences to tell my friends that they should drink some red wine in dinners.

Drinking wine has a lot of positive sides that [depend / depends] on which type of wine people purchase, for example, some doctors have recommended people drink red wine because they are better for health.

I have stopped writing after this sentence, because I am not sure whether I should use a singualr verb or not.
Here is the reason why I hesitate:
Drinking wine is singular, but a lot of positive sides is plural, so I am confused.

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    You have to ask yourself what depends on what. Is it positive sides that depend on the type of wine people purchase, or is it drinking wine that depends on the type of wine people purchase? Furthermore, it's grammatically amiss to refer to red wine as they.
    – user3395
    Commented Jul 14, 2017 at 9:31
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    Instead of positive sides you can use the word benefits. And do I still get the benefits if someone else buys the wine? :)
    – TimR
    Commented Jul 14, 2017 at 11:10
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    @Tᴚoɯɐuo isn't that a double benefit? :)
    – Andrew
    Commented Jul 14, 2017 at 15:00

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As userr2684291's comment points out, it depends on which noun is the subject of the verb "depend". Is it "drinking wine" or is it "many side [effects]"? You can go either way:

Drinking wine has a lot of positive effects, and depends ...

Drinking wine has a lot of positive effects that depend ...

However, the rest of your sentence makes it clear that it's the effects that vary depending on which wine is drunk. So go with "depend".

Also, it's difficult to think of a sentence in which the gerund "drinking wine" can depend on anything, but let me give it a try:

Drinking wine with friends depends entirely on whether there is wine to drink. If they bring the wine, they are my friends. If they show up empty handed, I show them the door!

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    @kitty also note my edited answer. Using "that depend" links effects to depend. If you want "drinking wine" to be the subject, you have to use a different conjunction.
    – Andrew
    Commented Jul 14, 2017 at 16:29

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