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yes phenol does show hydrogen bonding.the delocalized electron ring attracts the lone pair electrons of oxygen of hydroxyl group as along with the bonded electron pair of the o2 with the benzene ring.being more electronegative than the h2-atom it takes the bonding electron cloud in between towards him. so the total charge of the o2 atom rises to negative.so the o2 atom becomes negatively charged & the H2 atom becomes positively charged.they become polar and at this state phenols can make in between them & with the water too.in case of making H2-bond the spatial arrangement of hydroxyl group should let only to make bonds in between 2/3 phenol due to the steric body of benzene.in case of phenol only one side in a huge structure is capable to make H2 bond and the rest doesn't. but the delocalized electron cloud of benzene ring should make the hydroxyl polarization stable and it can also attract another body of benzene in phenol by arranging their spatial arrangement in such a way that they have opposite magnetic pole towards them originated due to the rotation of delocalized electron cloud within the benzene ring.these all are just my assumptions.

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