Bolted and riveted connections are a mainstay in many aerospace, mechanical, and civil engineering applications. Early detection of bolt loosening is essential for ensuring structural integrity and preventing catastrophic failures. Guided wave-based structural health monitoring (SHM) systems are well-suited for damage detection in plate-like structures. The present study aims at an experimental investigation of Lamb wave propagation in an aluminum lap joint with two bolts using piezoelectric transducers and compares the effectiveness of different damage indices based on wave energy transmission between plates in looseness detection. Torque values ranging from 5 Nm to 12 Nm at 1 Nm intervals are applied, along with a hand-tightened condition as well as free plates without bolts. Torquing conditions are evaluated for both bolted joints individually as well as simultaneously. The experiment is currently in progress, and the preliminary results are being examined. Further to this, the experimental findings will be compared with the finite element (FE) modelling results. Relatively few studies have explored the use of deep learning algorithms to enhance the performance of guided wave-based SHM systems for bolt loosening detection. The central goal of this study is to develop a neural network architecture for a Lamb wave propagation-based SHM system for bolted connections. This network will be trained using damage indices from the FE modelling results and later validated with the experimental data.