Is It Time to Lower My Dating Expectations or to Just Stop Dating?

It’s time to evaluate how we’re dating, and why.

As this is not my first day on planet Earth, I know how dating is supposed to work. It’s not like I haven’t seen the movies. One person meets another in person or online, they talk, and then a date is scheduled. There is an event. A drink. A dinner. Maybe even a movie. There’s time spent together, and it’s either hell and you avoid that person forevermore, it’s heaven for one of you and the other person ghosts, it’s cool for both of you but neither of you is feeling it for a repeat engagement, or it’s awesome and you both want to repeat the experience with another date.

In a moment of raw honesty, I’ll confess something true but sad. I’ve been stood up for more dates than I’ve ever actually been on. I’m sure I’m not the only human who can say this, but I feel like it some days. When I was younger, the guys I met were mostly into “hanging out.” I think we all know what that means. Even if you didn’t sleep with them (and I didn’t), they didn’t want to have to plan a date, pay for a drink or dinner, or commit to being seen with you in public just in case they had some other options going on the side. I tried to be the cool girl who was okay with it, but I always felt wistful when I saw couples going out on actual dates.

In college, I was done with just hanging out. I didn’t want to be the one that never got taken anywhere. So, I tried dating. I went out on a few. If I’m honest, most were anxiety-provoking experiences with mixed results. Sometimes, I didn’t feel safe. Other times, I felt painfully bored. Even in the best-case scenario, I was wracked with nerves. I kept asking myself: Is this dating then? I just wasn’t having a good time.

Then, I got married young, which is something some of us do when we have low self-esteem and finally find a partner who sticks around for longer than three months. I put all my eggs into that particular basket and decided to make the best of it. My incurably romantic heart died a little, but I did what I felt I had to do.

After my inevitable divorce, I realized that dating could be fun. There was the coffee date with the charming man who made me laugh — and who I dated for a little while before he fell in love with someone else. There was a game room date night with another handsome companion who later turned into a great friend. I’ve had dates that were interesting and cringe-worthy dates, but most of the time, I’ve had conversations that went nowhere with no dates to follow.

I guess what I’m saying is this — do I need to lower my standards, or is it time to just give up and stop trying to date?

I like myself now. I’m not the same insecure person I was as a teen or in my twenties. I’ve got my own house, a couple of kids, and some pretty precious pets. I’m working my dream job, and if I sigh every single time that I read a romance novel or watch a rom-com, I know I’m not alone. There are even married women out there sighing right along with me — I know because I used to be one of them.

But dating isn’t happening as it does in the movies — not for me anyway. I know better than to lower my partner's expectations at this point in my life, but I wonder if I should adjust my dating expectations. Are we supposed to just ask about each other’s day until one of us dies? Is that dating now?

Pardon me for wanting romance — or at least a tiny bit of effort. Right now, holiday pop-ups are happening all around me. How easy would it be to meet someone at a place positively bejeweled with lights and decorations to have a drink and conversation? In my opinion, dating options are so plentiful that it absolutely could not be any easier, and yet, I’m finding the people who want to “hang out” or simply talk forever and never meet.

Are My Dating Expectations Reasonable?

I started to evaluate my dating expectations. I’m not expecting every single date to be magical and perfect. I do expect that the person who agreed to the date show up for it. That seems fair enough.

I’ve stopped interacting with people who suggest hanging out as the first meeting. I’m not doing it. I’m happy to meet with a prearranged plan, but I’ll not be visiting anyone’s house on a first meet-up as I have no interest in starring in a true crime podcast now or ever.

I even am happy to be the one to suggest the date. I don’t sit back and wait for the man to initiate. I’m happy to be the one to suggest a plan and make an effort. But most of the time, I notice people don’t want to fix a specific date or time, and as a single parent, I can’t make spontaneous, last-minute plans. Honestly, even if I didn’t have children, I would not be okay with that. My life is busy, and I’m not just going to abandon all my plans to meet someone who couldn’t decide until the last minute if they even wanted to meet me.

I believe that my dating expectations are reasonable. Meeting up for a drink or a fun activity is simple. It doesn’t require a lot of time or money. It doesn’t involve much commitment. It simply gives us a chance to vet our prospective partners and to have them do the same. I don’t know if that expectation can get any lower.

How Do I Know When It’s Time to Stop Dating?

So, then I think: Is it just time to stop dating altogether? Should I just raise the white flag and be done with it all? Because I’ll be honest: It’s disappointing to be this age and to admit that I’ve been stood up for far more dates than I’ve been on. It makes me think that the men of this world are quite horrible when the reality is being skewed by my experience. I don’t want to think of men as terrible, but I also don’t want to keep hoping for fun dates and then merely engaging with yet another pen pal. Or worse — yet another man who thinks his sexting attempts are charming rather than repugnant.

I’m single, and sometimes, I miss being in a relationship — the good kind anyway. I miss having a partner who is also my best friend. But since having a partner requires dating, it doesn’t feel like it’s in the cards right now. I’m tired of bringing all the effort, magic, and whimsy only to be met with monosyllabic responses and no effort at all to meet.

When It’s Not Fun Anymore

It might be time to stop dating when we’re not having any fun. I don’t expect my relationships to all be a laugh-a-minute, but I do think there should be something fun about the process of getting to know someone and enjoying their company. If I’m not having fun, why am I even doing it? Life is far too short to keep engaging in something that feels like a waste of time.

Honestly, this year has been one of the hardest I’ve experienced, which is saying something since I’ve had other challenging years. Some days, I am filled with anxiety, but I still know how to engage with other people in healthy ways. Dating could be something fun that feels good, but instead, it feels like one more topic of anxiety for the pile.

When Being Single Feels Pretty Good

I might be my strongest self when I’m single. It feels that way sometimes. I’m happy with myself and the life I’ve created. If I’m lonely sometimes, I know that I’m probably not any lonelier than someone in a bad relationship.

So, maybe I should stop dating until dating someone feels better than being single — and being single feels pretty good right now. It feels especially good in light of the messages that never go deeper than the surface. I have plenty of friends and interests. I don’t need dating apps to amuse me. Frankly, I am not amused.

When There’s More Trying Than Doing

The problem might be that I’m trying to date. I’m putting myself out there and making myself available rather than just existing and being available. I live in a small town, and it seemed like a good idea to increase my options. But I feel like I’m doing more trying to date than actually dating. So, maybe it’s not time to stop dating. Maybe it’s time to stop trying to date and just let it happen whenever it does.

I’m not a person who likes to sit around and let things happen. I’m the person who makes things happen. That kind of initiative has gotten me far, but it turns out that I can’t force a love story to happen by wish, will, or want. I have to trust the timing of the Universe and stop focusing on trying to force the timing.

To Date or Not to Date: That’s Not the Question

I’ve decided that it doesn’t matter if I do or don’t want to date. Dating isn’t happening anyway. I put myself out there. I took myself back out. I put myself back out there again. I feel like I’m playing hokey pokey here.

Frankly, I’m tired of thinking about it. It’s running like a hamster wheel in my brain. I plan solo dates and friend dates and take my kids out to have a good time at places I think would make cool date locations. I live my life.

I know I’m a pretty awesome partner. I’m playful with a wicked sense of humor, and I don’t try to be anyone but who I am. I’m generous to a fault, and even when I’m not perfect, I keep trying to do my best. I’ve got a lot to offer the right person, but it might be time to admit that the right person will come along when it’s time and not a moment before.

And when the right person comes along, I know that there will be dating. I don’t have to lower my expectations. I don’t have to quit being available. My expectations are reasonable, but I don’t want to keep endlessly trying while feeling like I’m getting nowhere. I’ll take a break until it feels fun again, and if it never really feels fun, then I know there are far worse things than being happily single.