The structure and spectroscopic properties of a diluted compound can be deeply affected by its interaction with the neighboring molecules of the solvent, and the associated solvatochromism is an effect that becomes more noticeable with the increase in both the dipole moment of the solute and the polarity of the medium. The correct description of the complex set of interactions that prevail in the solvation process remains a challenge for theoreticians not only when interpreting an observed behavior but also when considering the possible existence of novel properties in untested solute-solvent systems. On the basis of an ab initio study, we examine here how the presence of solvents of different polarities should affect the electronic properties of a family of molecules, formally related to Betaine-30 (aka Reichardt's dye), whose donor (D) and acceptor (A) groups are terminally connected to conjugated chains of different sizes. Because these molecules exhibit elevated ground-state dipole moment that should strongly interact with molecules of a polar solvent, a large hypsochromic shift is predicted for them. However, in a recent gas-phase study of these molecules, we have established the existence of an "inversion" in the spatial localization of their frontier orbitals when the size of the conjugated bridge connecting the D and A groups is progressively increased. This fact has led us to suggest that the increase in size of dissolved betaines should be accompanied by a large variation in their solvatochromic properties. In this work, we first use the self-consistent reaction field approach at the configuration interaction level to estimate the expected bathochromic shift in the absorption spectra (positive solvatochromism) in the largest members of the investigated betaine family when dissolved in different low polarity solvents and then discuss the conformational changes as a consequence of the solute-solvent interactions. We then use these results to interpret the observed solvatochromic properties of push-pull molecules of varying size and discuss the corresponding implications on their photochemical properties.