Are You Bummed Out Being Single?

Now that I’m married, I’m seeing my singlehood in a whole new light. I wouldn’t trade my husband for my single life; I don’t want to go back, but if I can’t help but think of the things I would do differently. 

I’m not nitpicking every misstep I made, I’m human. Even if I feel totally cringy about a particular guy now, in retrospect, I know that at the time it meant something to me. Bigger picture, though: I spent a lot of time feeling anguish. Anguish for not living the life I wanted to live, and for dating men that weren’t good enough for me to begin with.

I am naturally a strong, independent person and this is who I’ve always believed myself to be. However, when I was single I wasn’t thriving. I wasn’t depressed or unhappy, in the holistic sense, but I was ho-humming along hoping to find a special someone to thrive with. As if I couldn’t thrive all by myself. 

I’ve been married four years now, and I’m looking back with a new perspective. Even though I love my life now and I wouldn’t trade for my old life, I do sometimes think about the “woulda, coulda, shouldas.” 


I Wish I Read More Self-Help

Before I met my husband I’d been single for a long time. I’d never been married before and my long-term relationships weren’t really all that long in the grand scheme of things. My husband and I just celebrated our four year anniversary and it’s the longest relationship I’ve ever been in.

Our relationship started on fire and was not without ups and downs. I went from living by myself, with only myself to answer to, to a house with another adult and three young boys. I didn’t just marry a man, I married a full house. 

It was hard for me. I was used to being alone almost all the time. Unless I was at work or out with friends/family, I was alone.

Because of these new relationship dynamics, I sought help. I’m an avid reader, so naturally I turned to books. Self-help books became my new favorite genre. 

All of a sudden I was learning about boundaries, attachment theory, and living true to my authentic self.

This isn’t to say that I knew nothing of boundaries or being self-reflective or learning to “meet” myself, but I was rarely deliberate or intentional. I also have a go-with-the-flow personality, so yeah, people pushed my boundaries and I sometimes went against what I needed in order to feel like my whole self.

I’m so much stronger now that I’ve taught myself more about relationship psychology. I wish I was this strong when I was dating. 

Reading all these books have greatly helped me with my relationships with myself, my family, work and my husband. I know they would have helped me when I was single.

See Below For Book Recommendations.

I Wish Brushed Off Rejection, Ghosting and Those Sort Of Things

If I had read some of the self-help books I’ve mentioned I surely would not have cared as much when I experienced ghosting, breadcrumbing and otherwise rude dismissive behavior.

I would have slowed down and really taken the time to realize that I am better than the way some men treated me. In turn, something like ghosting would have had no effect on me. Or, at the very least, not as much as it did in some cases. 

If a guy I really liked rejected me, I would have dug deeper and thought about whether or not I really liked him, or just the idea. I would have come from a place of grounded thoughtfulness, instead of hopeless desire. 

Why did I care? Why did I let it bother me?

The truth is, it was about me, not about them. I wanted a deep connection with someone and when that dream didn’t come true, I let some lame behavior on the guys’ part get to me.

This point circles back to exploring more self-help and understanding relationship psychology. 

Overall, I felt comfortable with being single and I enjoyed my routine. But, not having dating work out for me was a struggle. And, I let it get to me, by way of giving the wrong men for me the power to make me feel bad about myself.

Only I should have the power over what makes me feel good or bad about myself.

Me, Oktoberfest 1998

I Wish I Traveled More


These days I sometimes think about how I’d love to just hop in my car and go somewhere. I’d pop on an audiobook, drive, and wind up somewhere I’ve never been before. Or, I’d book a plane ticket and spend a week at a beachy resort, drink cocktails, read books, splash in the waves and have a great time. All by myself. 

Why didn’t I? I wish I knew. I didn’t think about it. It’s not like I deliberately told myself, I’ll travel, but only once I find a man. It was more of an innate subconscious thing. 

Now I do have a man and we don’t travel much. When we do travel, it’s a big production with four kids in tow. It’s not just little ole me on a fall afternoon saying to myself: I’m going to go to Vermont this weekend to see autumn leaves and taste test maple syrup.

That’s what I wish I did more of. More spontaneous who cares if I’m by myself activities. For some, it might be the movies, or hiking, or going to museums. 

Not everyone is a traveler. My point is really about activities you’d rather do with a partner. Sure, I’d rather share travel memories with loved ones, but I should not have let that stop me from creating solo memories. If I had done that, then my thoughts right now would not be “I wish I had.” 

What things do you hold yourself back from doing because you feel awkward doing it by yourself? 

The truth is we don’t need to stop ourselves from doing things we are excited to do because we’re not coupled up. 



There is a notion of shame when it comes to being single, and it’s too bad. Singledom should be embraced.

We tend to have a “grass is greener” mentality. In reality, no matter what we are doing we are always not doing something else. We can’t do everything simultaneously. 

It’s like the gurus say: Live In The Now, Carpe Diem, Be Grateful For What You Have. 

I know living in the moment would have come much easier if I’d done the things I mentioned, and probably many other things I haven’t thought of yet. 

I’m not saying to pretend to love the things about being single that you don’t love. The desire to meet someone special is valid and a pursuit you are entitled to. 

It’s tough when the sense of lack feels overwhelming and all-consuming. However, being single does not hinder your capabilities, even if sometimes it feels like it does.

I let being single and dating get in the way of my confidence in myself and my love for travel exploration. 

Hindsight is 20/20.

Related Posts

Books I Think Everyone Should Read And How The Relate To Dating

    Your Cart
    Your cart is emptyReturn to Shop