Generating paired sequences with maximal compatibility from a given set is one of the most important challenges in various applications, including information and communication technologies. However, the number of possible pairings explodes in a double factorial order as a function of the number of entities, manifesting the difficulties of finding the optimal pairing that maximizes the overall reward. In the meantime, in real-world systems, such as user pairing in non-orthogonal multiple access (NOMA), pairing often needs to be conducted at high speed in dynamically changing environments; hence, efficient recognition of the environment and finding high reward pairings are highly demanded. In this paper, we demonstrate an efficient pairing algorithm to recognize compatibilities among elements as well as to find a pairing that yields a high total compatibility. The proposed pairing strategy consists of two phases. The first is the observation phase, where compatibility information among elements is obtained by only observing the sum of rewards. We show an efficient strategy that allows obtaining all compatibility information with minimal observations. The minimum number of observations under these conditions is also discussed, along with its mathematical proof. The second is the combination phase, by which a pairing with a large total reward is determined heuristically. We transform the pairing problem into a traveling salesman problem (TSP) in a three-layer graph structure, which we call Pairing-TSP. We demonstrate heuristic algorithms in solving the Pairing-TSP efficiently. This research is expected to be utilized in real-world applications such as NOMA, social networks, among others.