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It can be so awkward and make it hard for the entire group (I've been in that situation before) but I do think it's easier because I've usually always started out as friends with someone then got together mutually... but that can end badly too
Basically, all relationships are hard so just don't bother ahhahha
Nail and bail is always the best option
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In my latter years of high school we had a close group of about 15-20 people, I would say at some point everyone in that group had a relationship with one other person in the group. We all came through it and now I think only two of the group are still in their relationships.