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Je dois quand même avouer qu'il m'a fait vivre des choses à côté desquelles j'aurais pu passer.

I express this sentence in English as follows, and I suppose that « desquelles » serves the function of "that". But beyond that, I don’t know why the plain and simple « que » cannot be used here.

"But I have to admit that thanks to him I’ve been able to experience some things close by that I might otherwise have missed out on."

Con-gras-tue-les-chiens
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The sentence is "passer à côté de [quelque chose]", which, in English, is "to pass by [something]". It means, in this context, "to miss out on something". It is an integral part of the expression; in your translation you translated that part by "close by" which is not correct, it goes with "miss out on".

The "[quelque chose]" is, here, the relative pronoun "lesquelles". In English you would translate it by "which" or "that". It is contracted with "des" to produce "desquelles = des + lesquelles", exactly like "de + les = des".

Simply using "que" would have been incorrect here: "passer à côté" can only take an indirect complement. You cannot say "je suis passé à côté toi", you must say "je suis passé à côté de toi" (I passed by you).

So a correct translation of the second part becomes:

But I have to admit that thanks to him I've been able to experience some things that I might otherwise have missed out on.

PS: Maybe the French sentence is easier to parse (but doesn't really sound good) if you split it in half:

Je dois quand même avouer qu'il m'a fait vivre des choses. J'aurai pu passer à côté de ces choses.

I have to admit that thanks to him I've been able to experience some things. I might have missed out on those things otherwise.

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N.I.
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  • Thanks. Is the use of "dont" incorrect as well? « Je dois quand même avouer qu'il m'a fait vivre des choses dont j'aurais pu passer à côté. » – Con-gras-tue-les-chiens May 30 '16 at 16:05
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    @MasonH.Hatfield Dont can be a plural. I can't think of any singular/plural distinction in the usage of dont. In this sentence, it wouldn't work in the singular either: “il m'a fait vivre une chose dont j'aurais pu passer à côté” sounds just as wrong (it should be “… une chose à côté de laquelle j'aurais pu passer”). (I think that some French people might use dont* in informal speech though.) – Gilles 'SO nous est hostile' May 30 '16 at 20:27
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    @LUNA You can't use dont here. I had to look up why: TLF 1.I.B.a.α. If dont would be a complement of a noun that is itself has a preposition before it, then we use duquel (and feminine/plural variants) instead. – Gilles 'SO nous est hostile' May 30 '16 at 20:31
  • @Gilles Yes, you are correct. It is my mistake. Example: Voici les clés dont elles ont besoin. – Mason H. Hatfield May 31 '16 at 03:05