Feeling Depressed or Lonely After a Date

Feeling Depressed or Lonely After a Date

I took a woman on a date recently. It was fun, flirty, and memorable. Everything you’d want it to be. She's beautiful. A single mom of teenagers who works from home on a successful business she's built from the ground up.

I've only known her for about a month, but from what I've learned, she's active, involved, and never slows down. From early morning workouts to late night dances, homeschooling her children and providing for them in between, she's a lot like the Proverbs 31 gal you read about, sans the husband.

When you imagine a strong independent woman whose ex left her for poorer choices, she's that quintessential image.

The date was more like a combination of three dates in one night. Yet, it wasn't the chemistry or competitive banter we had while rock climbing, or the great conversation over pizza and beer, nor was it the live salsa band and Latin-speakeasy-salsa dancing afterward that has me writing about it.

It was the text I received the morning after.

But before I get into that, you should understand why it was so unexpected, plus my theory as to why it happened.


In dating, and in life, when we meet someone new, we typically accept them as they present themselves. And as a rule of thumb, most people I run into have their stuff together, at least on the surface. Busy bees running around, doing great things, growing businesses, volunteering at charity events, out having a good time with friends.

I think it’s natural to perceive others positively. After all, it’s how I hope to be received. That's what we all seem to be striving for, right? A healthy reputation – giving off a positive "vibe," as it were.

And to be clear, there is nothing wrong with that. We should be spending our time wisely as individuals, in whatever circumstance we find ourselves – single mom or otherwise. It's commendable. If we aren't redeeming the time we have on this earth, then what are we doing with it?

Nonetheless, from our own limited point of view, from the outside looking in on a person's life of which we know little about, we're often more caught up in our own assumptions based on what we see and the biases we carry. For example, if she's strong, beautiful, and successful, we may assume she isn't in need of a man's love. At least that's what we're sold on television, the Internet, and social media.

Take that a bit further. Not only are we caught up in our own assumptions of who others are or what they want, but we’re often caught up in our own devices (and I don’t mean phones). We get caught up in our immediate desires, tricks, insecurities, and other methods that tend to rule our hearts and minds, frequently convincing us of false realities.

But let’s save that rabbit hole for another day.

Suffice it to say that women must be tough these days, and reliance on men is weakness. Or so the narrative goes.

And it's no wonder that women feel this burden, what with the current state of men. Chivalry is all but forgotten. The hypersexualization of society, normalization of hook-up culture, and ubiquity of pornography for both genders has led to an unfortunate acceptance of behavior that was once considered taboo.

The hope for what a man should be is so rare, now, that an actual encounter with one may solicit fear. After all, what should a woman think in a circumstance like this? The hope of every love story she's ever fantasized about from a little girl has faded over time – the hope that she can someday bask in her feminine energy – dwindling with every weak man that opens his mouth. It is no wonder she carries on as she does, strong and busy.

Yet, if or when that hope is rekindled, what effect does it have?


All of this came to mind after receiving that text the next morning. And, who knows? She may not have enjoyed the date as much as I did. And that's fine. Rest assured, I'm no Casanova on a white horse. But thankfully, I’ve got a commitment for a second date.

Furthermore, this wasn't the first time I’d witnessed a woman experiencing loneliness after a date. I've dated single moms before. The last one I dated seriously was 10 years ago. She also had two kids with an absent father. I remember the sadness in her eyes sometimes.

I believe that single women have a tangible desire for a helper, a soft place to land. Carrying the entire burden of a family is heavy business, year after year. Sleeping in the same lonely bed gets old as the kids get older. The want for companionship is never far from the heart, no matter how hard the shell may be that hides it.

And why blame them? No doubt the life of a single mom is rewarding and enjoyable, but the need is still very real.

I also believe it can be an emotional vulnerability for single moms, one that too many men exploit for their own selfish ends. In my experience, it takes very little to open that old wound inside a woman. And if it isn’t tread carefully, it can be quite painful for her.


The last thing I’ll mention is that there were two things that stuck out to me about her message:

  1. That she felt the need to tell me this (I believe everything a woman does is a test whether she realizes it or not.)
  2. It happened the morning after a date in which we had a lot of time together to open up with deep conversation.

Now, you might be thinking, “She probably just had a bad morning, started her cycle, or something was just off. It could have been a million other things.” And that may very well have been the case. We spoke about it, and I offered her the opportunity to chat about it, but even she couldn’t make sense of it that morning.

Whatever it was, it isn’t my intention to take credit for it nor to deny that I had anything to do with it. Her feeling of loneliness, that is. Rather, I thought it worthwhile to reflect upon as a beautiful example of the affect we can have on each other when we least expect it, especially in dating.

Connections can be powerful.

This was the message I received the morning after our fun date:

"Ever have a super lonely day, even if you're around people?"
"I'm getting beaten over the head and neck with that feeling today. Almost to tears."
"Me. Tears. Eww."