Let $X$ and $Y$ be any two graphs of order $n$. The friends-and-strangers graph $\mathsf{FS}(X,Y)$ of $X$ and $Y$ is a graph with vertex set consisting of all bijections $σ:V(X) \mapsto V(Y)$, in which two bijections $σ$, $σ'$ are adjacent if and only if they differ precisely on two adjacent vertices of $X$, and the corresponding mappings are adjacent in $Y$. The most fundamental question that one can ask about these friends-and-strangers graphs is whether or not they are connected. Let $\mathsf{Lollipop}_{n-k,k}$ be a lollipop graph of order $n$ obtained by identifying one end of a path of order $n-k+1$ with a vertex of a complete graph of order $k$. Defant and Kravitz started to study the connectedness of $\mathsf{FS}(\mathsf{Lollipop}_{n-k,k},Y)$. In this paper, we give a sufficient and necessary condition for $\mathsf{FS}(\mathsf{Lollipop}_{n-k,k},Y)$ to be connected for all $2\leq k\leq n$.