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A fully conjugated figure‐of‐eight nanohoop is presented with facile synthesis. The molecule's lemniscular skeleton features the combination of two strained oligoparaphenylene loops and a flexible cyclooctatetrathiophene core. Its rigid yet guest‐adaptive cavities enable the formation of the peanut‐like 1:2 host–guest complexes with C60 or C70, which have been confirmed by X‐ray crystallography and characterized in solution. Further computational studies suggest notable geometric variations and non‐covalent interactions of the cavities upon binding with different fullerenes, as well as overall conjugation comparable to cycloparaphenylenes. [ABSTRACT FROM AUTHOR]