What's normal and natural to some can be excruciating and horrific for others. For those who dated for a short amount of time or had little drama within the shidduch realm of their lives, it's hard to imagine how painful it can be to those who weren't so lucky. Aside from living in a space where they feel stuck, in limbo, unsettled, and unable to move forward, often singles feel like they don't have a place in frum society. As a community we value family structure, and for a good reason the norm is the nuclear family. It's a Torah value.
It is a primary developmental need to connect intimately with a partner, as per meeting developmental psychologist Erik Erikson's "intimacy vs isolation," stage or getting stuck and being unable to move forward in life. The Torah tells us "Lo tov heyos adam levado." It's hard for anyone to be alone, and this challenge applies to single boys as well, but Jewish women especially were created with a strong desire and need to connect and nurture. Unable to share this connection with a spouse and their own families, it's an everyday struggle. It's lonely no matter how many things they're involved with and how many close friends and family members they have. There is something one can only get from a close intimate relationship.
Taking all this into account in addition to how painful it can be to meet and date promising prospectives and the aftermath of it not working out (sometimes over and over and over again), investing immense emotional energy and being left with nothing if it doesn't pan out, let alone the physical expenses, be them time, money and/or travel. Added together with the hurtful comments from people who mean well but don't understand, the people who don't think at all, the unwanted pity, you name it, (older) singles experience quite a bit of pain throughout the parsha.
Perhaps a single is healthy B"H, has so much going for her/him, etc., and the only thing is she’s not married, but it's real pain. It is well known that the part of the brain that's associated with physical pain, the anterior cingulate, is the same part of the brain that is connected with emotional pain. This pain is just as hard. Some of the pain is the loneliness, the feeling of not fitting in, the perceived judgements, the burning desire to give/nurture/connect, the countless disappointments. But there is also the fear, the not knowing when or if I will ever meet the right one and get married, ever fit in, ever be able to move forward in my life.
As a society we look at anyone that doesn't fit the norm as deviant. We try to figure out why or how they don't fit the mold. Perhaps it's a survival tactic, we want to fit in, so we have to make judgements about people who are not like the majority in whatever way. We often unwittingly stigmatize and judge, sometimes with devastating consequences. Singles don't want your pity. They aren't nebachs. They just want support and care. Treat her like a person, being single isn't her only piece of identity.
