I will approach your problem from a pure mathematical perspective:
Let me first say that in your post you use the same notation $\dagger$ for two distinct mappings which have two different definitions and notations. One mapping acts on the space of linear densely defined operators in a complex separable Hilbert space and the other mapping is from the Hilbert space itself to its (topological) dual with respect to the topology induced by the norm (this mapping assignes a vector to a continuous functional). The first mapping is regularly denoted in physics by the dagger $\dagger$, while the second one by the tilde $\widetilde{,,,}$
Let me redefine your statement to be proved by using proper mathematical notation and dismissing the mathematically complicated Dirac braket notation. You wish to prove that for a self-adjoint $A:D(A)\subseteq\mathscr{H} \rightarrow \mathscr{H}$ we have the following equality of functionals:
$$\widetilde{A\Psi} =A^{\times}\widetilde{\Psi}.$$
Denote by $ F_{\Psi}\in\widetilde{\mathscr{H}}$ a continuous functional on $\mathscr{H}$ assigned to an arbitrary vector $\Psi\in D(A)\subseteq\mathscr{H}$. We then have:
$$\widetilde{A\Psi} (\varphi) \equiv F_{A\Psi} (\varphi) = \langle A\Psi, \varphi\rangle = \langle \Psi, A^{\dagger}\varphi\rangle = \langle \Psi, A\varphi\rangle, ~ \forall \varphi\in D(A)\tag{1}$$
- Turning to the right hand side, $A^{\times}$ is called the dual operator assigned to a linear operator acting in the Hilbert space ($A^{\times}:\widetilde{\mathscr{H}}\rightarrow\widetilde{\mathscr{H}}$). We then use its definition:
$$ \left(A^{\times} \widetilde{\Psi}\right) (\varphi) =\left(A^{\times}F_{\Psi}\right)(\varphi)=: F_{\Psi} (A\varphi) = \langle\Psi, A\phi\rangle, ~ \forall \varphi\in D(A) \tag{2} $$
From $(1)$ and $(2)$ we obtain what we needed to prove.