Lessons I’ve Learned in 6 Years of Singleness

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This year for Valentine’s, I’m forgoing the whole Galentine’s Day / Me-Day thing. I’m convinced that you don’t need a Single Girl’s Survival Guide for Valentine’s Day. Tonight I’m opening up a bottle of wine, and I’m getting really real. If you’d like to have a glass, too, I’d love that.

I guess I’ll start by explaining because I’m betting that a few of you looked at the title of this post and thought, huh?  Nope, there’s no typo or correction needed. This summer marks six years of me being single, and if you think that is a long time, try living it. In six years, I’ve been on countless dates and fallen for just a guy or two {but definitely no more}. After the last guy I really liked, I prayed that God would keep me from relationships that would ultimately result in heartbreak. My only explanation is that that seems to be his plan. I’m honestly not sure how I feel about putting this out there. And I’m not gonna lie, this feels a bit like I’m letting you guys read my {nonexistent} diary or something. It’s really weird, but maybe we’ll all survive this.

By now, I should be an expert on singleness right? {HA, lol no} But here’s what I’ve learned.

No. 1 | Trust your gut

I remember my senior year of college telling my roommate Jane that I thought I liked a guy in our friend group. I’ll never forget her shock. She got quiet and serious and leaned in a bit. Caroline, you don’t like anybody. This is kind of a big deal. And she was right. Now, what she meant is that I like next to no one when it comes to dating. I generally like people, in case I needed to clarify. There are pros and cons of being this way. Pros: it doesn’t take me long to decide whether or not I could possibly date someone, so we waste the least amount of time possible. Cons: I absolutely hate going on dates. I know I have to. I know it’s part of the process, but I’m never excited to go on a first date because I’m not expecting to like the guy. However, if I think that if there’s maybe a chance, I go on the date because everyone deserves a shot, right?

No. 2 | I know what I want

Between dates, can-I-buy-you-a-drink‘s, and long talks with friends, I’ve learned what I do and what I don’t want. I think it’s part of the reason why I like so few guys. It doesn’t come from a place of judgement or being jaded. It’s a result of getting really clear on what I want and understanding what kind of person I need. I need someone who is outgoing, protective, thoughtful, and compassionate. It’d be nice if he were tall and handsome… and athletic… and tidy, but those aren’t needs, are they? For me, singleness has been a natural result of not wanting to waste anyone’s time or emotion on relationships that we both know are not headed toward marriage.

No. 3 | I really value my alone time

…and my social time. In college, it wass easy to be social. You could walk everywhere, there’s always something going on, and there are always 20+ people to make plans with. It wasn’t until after I graduated that I realized what an introvert I am once the context and complications of real life are factored in. When my best friends lived in Dallas, it was girls night at least once a week, but I’m not as big on going out. I always have a great time when I go out, but sometimes, I have to make myself. One of my goals this year is to exercise that social muscle and get to know new people because that’s one thing I really miss that about college. Understanding where I value my time is important for two reasons: One, I need to date someone who is considerate of that. I need my alone time, but I also need time to just be with friends. And two, I’ve always thought that being content alone and being able to enjoy time by yourself is necessary before you can be in a happy relationship. I’ve just had a little more time than I bargained for.

No. 4 | Singleness challenges your confidence

All my single ladies, how many of you have felt behind? Like everyone in your friend group is taken but you? Everyone’s either having kids, married, engaged, or in a serious relationship. You wouldn’t know where to find a roommate if you tried. When you’re single, you don’t have any of those things to hide your confidence issues. There is no built-in cheerleader. In fact, your singleness amplifies insecurities. I can’t tell you how many times I’ve thought to myself what the hell is wrong with me? Why is everyone else getting married but me? There are definitely moments when you think the whole “Any guy would be lucky to have you – it’s just not your time yet” speech is complete B.S., especially since the person giving it is usually either your mom or someone who happens to be sporting a 2 carat rock. *eyeroll* No matter how patronizing it feels, it’s the truth. Our time will come.

No. 5 | I’ve been too nice

As women, we’ve been taught to be nice, to do as little as possible to rock the boat. After my first relationship, that was me. The cool girl, the laidback girlfriend, the go-with-the-flow gal. That’s my personality anyway, but part of me always wanted to be the cool girlfriend – low maintenance and easy to deal with. At least I always see who someone really was. If I was laidback, I could see someone’s true character and intentions. I had a clear picture of what they considered an appropriate way to treat me, because I wasn’t imposing my own ideas on them. You know where that got me? Getting ditched by my boyfriend on my 20th birthday to go drink with the boys. Six years later, it feels like a small thing, but at the time it was absolutely humiliating. That most definitely wouldn’t fly today. I’ve watched girls treat their boyfriends in a way that I would describe as bitchy and in return, be treated like queens. It’s not because they’re bitchy. It’s because they have hard, unchanging boundaries. Now I just want to clarify, 99.9% of the time, that relationship was incredible. Truly. But that little birthday mishap happened because I didn’t have clear, communicated boundaries and standards. You bet I do now.

No. 6 | Life doesn’t begin when you get married

It doesn’t?! It’s easy for any of us to think I’ll be happy when… {I have a boyfriend, I get engaged, I get married, I buy my first house, I have kids, etc.}. I’m convinced that all of us think this way. Happiness is just around the corner. I’m almost there. The truth is, life is already happening. It just doesn’t feel like it because that’s not how we treat it. I’m disappointed when I ask newlyweds how married life is, and they almost always respond that it’s “not that different.” While that might feel like a huge let down, it encourages me to not live like happiness is just around the corner, to stick to my values, and live for today.


Be encouraged. Show kindness. Exhibit love.

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