Getting in a New Relationship After Being Single Forever

This post has been in the back of mind for awhile now. I’ve wanted to write it several times but then thought against it. I finally realized that this is a blog about my life. It’s my journey through my late twenties and now my thirties. I’ve written so much about my shitty dating experiences that I should also include when things are going well, right?

I wrote once about a new man in my life and that ended shitty. I think that was part of the reluctance I had when it came to writing about a new relationship. But me and my man have been together for a little over 6 months now. He’s a big part of my life and this is a lifestyle blog. It makes sense that he’s going to come into conversation one of these days. He just met my parents for the first time two weeks ago so now it’s time my lovely readers meet him.

I may love broadcasting my entire life on a public blog but I recognize that not everyone may feel this way. That’s why I’m going to refer to the lovely man I’m dating as JR. (It’s part of his initials so it works.)

When people ask how we met, I usually say, “We went to High School together and recently reconnected.” All of this is true. But I am just leaving out certain aspects. By recently reconnected, what I really mean is found each other on a dating site. That’s right! Sometimes OK Cupid can work.

I was on OK Cupid for a very short time when JR messaged me. I immediately recognized him from High School. Before he even messaged me, I was on the brink of deleting my account. I had had enough of online dating. So after only exchanging a couple of messages with JR, I told him I was deleting my account and asked if he’d like to exchange numbers. I normally don’t do this. I like to talk for a little before exchanging numbers. I also usually just wait until the guy asks for the number. But in this case I knew that I would be deleting my account and I knew I didn’t want this to be the end of my interaction with JR.

So we exchanged numbers and I waited for him to contact me. He did; the next day. We spoke for a few weeks, met up on May 12th, and have been dating ever since.

It’s been really nice. And a lot of fun. But it’s also been a lot of adjusting. These past few years, even when I had someone, I still wouldn’t call myself taken. I was always single-ish. This is the first time in forever that I’m 100% not single. It’s been a little weird. Mostly awesome, but a little weird.

When you’ve been the single girl for so long, being in a relationship definitely takes some getting used to.

I’ve been lying to myself in the past. When I was dating, I would give myself a 2-date rule. I figured that it would take more than one date to determine if I actually liked someone. Two dates should let me know for sure. Well, after my first date with JR, I knew 100% that I liked him and wanted to go on another date. I also lied to myself with some past dudes and made excuses for them. I convinced myself numerous times that the guy really did like me. He just needs time. He’s really busy. And so many more excuses. I was lying to myself. If a guy likes you, you’ll know it. If a guy wants to be with you, he’ll make time. It’s really very simple. I just made it way more complicated than it needed to be.

The word boyfriend feels weird. It took me 6+ months to share JR with you guys. When I’m dating someone, I tend to keep them to myself for the most part. It takes a lot for me to share the guy with other people and talk about him. If he does come up in conversation, he is usually referred to as “this guy I’m dating.” The first time I spoke about JR and called him my boyfriend, it sounded weird. It still feels a little weird. It’s just a much easier term to use than “guy I’m dating.”

But girlfriend is a nice one to hear. Not gonna lie, it’s nice being introduced as “my girlfriend.”

Holy Batman! There is not enough time. Work and friends and family and alone time was already a lot to juggle. Adding a relationship has made maintaining everything overwhelming. It’s something I am still working on. There is never enough time to do everything I want.

Alone time is so much more satisfying. I love alone time. I loved my alone time when I was single. However, when you’re single, alone time isn’t always a choice. Alone time comes cause you have nothing else to do. Since being in a relationship, my alone time has become significantly more satisfying. I adore the nights spent in my apartment alone laying on the couch and watching TV for hours.

Doubt doesn’t magically go away. After so many dating mishaps, it’s easy to be skeptical. Too many times I have grown tired of the person I was dating or slowly realized that they were growing tired of me. I am pretty secure in my relationship with JR and don’t usually question where I stand. But this does not mean that doubt hasn’t gone away completely.

Sometimes clichés are right. When you’ve been single for awhile, you’re going to hear a lot of the same things. “It’ll happen when you least expect it” is one of those sayings I heard the most. I always thought it was ridiculous. I am single but would like to find someone. In some way, I’m always looking. But now I kind of know what they mean. The first time I met up with JR, I did not want to go. I had just had a huge dinner for my nephew’s birthday. All I wanted to do was go home and sleep. I remember throwing some mascara on in my car right before I walked into the bar. Before the date even started, I was already thinking about how and when I could leave. I did not expect anything to come of it.

Fear is one of the biggest enemies. Being single is easy. Being single is safe. You only have yourself to worry about yourself. You’re not giving someone else the capability to seriously hurt you or let you down.

Relationships involve a lot of talking and compromise. As a 30-year-old single person, I was very set in my ways. I was used to being on my own and not having to rely on anyone. I never had to think about anyone else, ever. Those views don’t always make for the healthiest of relationships. I had to become reacquainted with having a new person in my life.

All those disasters, make this relationship a lot sweeter. Man was I fed up with dating. You guys read all about it. I wasn’t kidding when I said that dating shouldn’t be so exhausting. I was tired of it! I was done with dating sites, first dates, unanswered texts, etc. Knowing how horrible things could be out there in the dating world and knowing how difficult it is to find someone you really connect with makes my relationship with JR that much sweeter.



  1. I relate to basically everything you said in this post! My boyfriend & I have been together 8 months now, and although I had dated other guys before him, they weren’t really…serious. So I’m in the first serious relationship of my adulthood(I’m 25). It definitely was, and sometimes still is, an adjustment bc I was so used to just worrying about myself. It’s a happy adjustment though 😊 I wish you and your man the best!

  2. Oh my goodness, oh my goodness, OH MY GOODNESS! You don’t even know how happy this makes me, hon! You deserve to be happy. You also hit the nail on the head when it comes to the ups and downs (and adjustments) you go through when the ‘ol relationship status is changed. While I haven’t had such luck, I’m hoping your point about the cliches being true is right haha.

    1. I really HATE the clichés. I heard SOOO many of them while I was single but sometimes they really are true. You are so friggen awesome. You deserve to find someone just as awesome as you. After seeing so many amazing girls remaining single for a significant amount of time, I’ve come to the conclusion that the more awesome you are, the longer it’s going to take to find someone to match your awesomeness.

  3. Love this, Liz! I’m in the exact same situation. I met my boyfriend (fuck that does sound weird even typing that out after being single for so long!) in high school and we basically kept in touch over the past 10 years until the time was right. Our first date was in August and I was a bit skeptical as well. It really does happen at the most unexpected time. 🙂

    1. Waiting so long was probably the best idea. I know for myself, if my dude and I had dated back in High School, it never would have lasted. We’re dating now at the right time.

  4. Hahaha oh my gosh, I met my guy on OKC too! I recommend it to friends, as I feel like it’s one of the best dating sites (Despite having a million creepers too). 😛 I’m soooooo happy for you and think you deserve such a great guy! I can’t wait to read more about him and what’s going on in your life. Congrats, girl!! ❤ (Is that weird to say for getting an awesome boyfriend?)

    1. Out of all the free dating sites, I think that OK Cupid is the best. It just seemed to have better caliber men. Even when things didn’t work out with the guys, I never had any horror stories from OK Cupid.

      1. I can see that happening. Most single people are one more than one sight. So I feel like even if someone is on Match you can find them on a free dating site as well.

  5. Yes! I am so happy for you!

    Having been constantly single until the past year (or at least single-ish), I completely relate to all of these. Saying ‘boyfriend’ has only just stopped sounding funny. And definitely having even less time than before can be tough. That’s when you know it’s right though – when you’re willing to rearrange an already good life because you’ve met someone who just might make it even better.

  6. Lol I totally know what you mean about “boyfriend” sounding weird. I thought I was the weird one for feeling that way. Anyway, best wishes for you and JR! Also–happy holidays!

  7. I’m so happy to finally hear about JR and that you two are still going strong. I understand your apprehension to write about him. But it was great to hear the perspective from “one of us singles,” recently committed. You’re at a place where you can still relate to us single ladies and share some wisdom and reassurance with us. I appreciated this post and found !

  8. Reblogged this on mind JO business and commented:
    Support “REBLOG” Sunday Ep.25: It was great to hear a perspective on singledom vs in a relationship from “one of us singles,” recently turned “committed.” Liz is at a place where she can still relate to us single ladies while sharing some wisdom and reassurance with us. Enjoy!

  9. Thanks for the insight. Most of these sound like things I’ll be going through whenever I finally get one of those boyfriends. lol

  10. A lot of what you wrote was me in my 20’s.

    The idea of having a girlfriend was great but the reality was exhausting. I loved my free time. I was the one you could have a lot of fun with from Thursday to Saturday but on Sunday I was ready to say goodbye.

    It’s a dangerous habit to get into unless you’re okay with being alone when you hit 40.

    It’s great that you gave him a chance and that you listened to that inner voice that something special was going on.

    Now that you’ve shared the big news with us this has become a wonderful happy ending, or a wonderful beginning I should say. 🙂

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