Diammonium diamantane-based guests demonstrate the highest affinities reported to date for 1:1 host-guest complexes. However, supramolecular chemistry of advanced analogs remains underexplored. Multitopic guests, composed of binding motifs exhibiting distinct selectivity towards different hosts, are pivotal components of molecular devices such as catalysts, sensors, drug delivery systems, and memory units. Our preliminary results with cyclodextrins (CD) and cucurbit[n]urils (CB) indicate that diamantane cage extended with rigid hydrocarbon moieties (ethylene glycol dimethyl ether, EDM) can form binding sites tailored for pairs or triplets of tightly packed hosts. Thus, we aim to prepare model guests based on EDM to thoroughly examine their binding abilities, i.e., the number, type, and mutual orientations of CB and CD units. Further, we will synthesize guests comprising EDM and other high-affinity binding sites to elucidate whether the binding modes at EDM can be affected, altered, or switched by other macrocycles. Acquisition of this fundamental knowledge will profoundly impact the design of supramolecular devices.