Is there any place in frum dating for a “casual” date – that is, a date on which one need not dress formally (a suit and tie for a boy and an outfit for a girl), but one can dress more casually?
Before directly addressing the inquiry at hand, I believe we should begin by identifying the value of dressing so ceremoniously on a date in the first place. And as I understand it, there are three salient reasons for doing so.
1. When entering or involved in the courtship process, one is generally best served by looking their sharpest, and by and large, people present optimally in formal garb.
2. Typically speaking, it feels nice to look nice. Deriving satisfaction from one’s presentation breeds confidence, and it is always advisable to date from a place of self-worth, rather than from a place of complacence or low esteem.
3. Going out on a date is an auspicious event that carries consequence. Hence, it is fitting to don garments of distinction as a display of deference to the import of the occasion, and in a show of proper respect to one’s counterpart.
That said, while in the majority of cases there is a great deal to be gained by the efforts taken to put oneself together to the utmost of one’s abilities, nonetheless, there are also exceptions to every rule. And thus, there are surely scenarios where a natural appearance may be the ideal route. For example, if both parties feel notably uncomfortable when draped in their finest apparel, dialing it back a notch might enhance their chances of a successful first date. Similarly, if a couple has gone out a few times, and they are still somewhat stiff when together, introducing a relaxed approach might be called for.
This is not to say that in these circumstances dressing down is the option, but that it may be an option. The overall point being, if one is cognizant of what there is to be achieved through dressing formally, and why that method is ordinarily the norm, one can then effectively assess when this practice is counterproductive, and when departing from standard protocol affords more favor than adherence has to offer.
May the Levusho Tzedaka ensure that we are all are motzei chayn v’chesed b’enei Elokim v’adam.