Dating and Insecurity (Plus an Overdue Update)

insecurities insecurity in dating love relationships emotional baggage divorce


It’s been three months since last I wrote but it feels like three days when I think about the speed at which the time passed. My full time job and kids and boyfriend keep me busy and then I’ve got a part time job on top of that, adding a fantastic 20 more hours of work per week. This is not a complaint, though – I am one of those people who thrives on a bustling life and, as a divorced mom, the extra income around the holiday season from a second job is more than welcome.


Greg and I are still together, and all is wonderful except for two things. One – his ex, who knows no boundaries and two – my insecurity, which knows no boundaries.

I won’t go into detail about his ex right now even though I’d love to share all the horrible things she does and says to him and their children. But right now let’s focus on me and how messed up I sometimes feel, okay?

Let’s recap a little. My first boyfriend in high school cheated on me. I found out because he called me by this other girl’s name one night and the next day a classmate told me she knew he had another girlfriend at another school. Yay. My ex husband begged me to come back after I asked him for a separation. I did, thinking at least for the kids’ sake we should give things a second chance. I found out a few months later he was carrying on a clandestine texting/FB relationship with his high school crush. Then I discovered that Tiger, the first person I went out with after my divorce (though, I must stress, we were not in a relationship) lied about me being the only woman he was seeing (there were at least two others). Which was particularly lame because I wouldn’t have cared if we’d stopped dating. Stupid boys.

Knowing what kinds of betrayals other women have gone through make these issues seem small in comparison, but then I have my marriage to Kyle, which left me feeling less significant and more downtrodden year after year. I lived each day wondering what I’d done wrong to so displease my husband. His interactions with me, especially after we had children, seemed mostly geared toward making me feel like an unintelligent failure.

And then I met Greg. I wrote about how, for the first several months we were dating, I had none of the doubts and insecurities that plagued the early parts of my first relationships. I felt so comfortable with him, so secure.

Until about five months in. Suddenly I started doubting how he felt about me. I thought, “This can’t be right that things are so wonderful, nothing is this great – he’s probably going to leave me. I’m not good enough. He’ll find someone prettier/thinner/with a better job/with fewer children/younger and then I’ll be history.” It’s like I couldn’t stop the thoughts from entering my head. And once I let those thoughts in, I felt like I could see evidence of his diminishing interest in what were, truly, innocuous situations. He didn’t reach for my hand quickly? He must be breaking up with me. He wanted to spend one night reading and not with me? Maybe that means he’s got a date.

Some friends said, “I’m sure everything is fine! Be positive!” Which makes a great poster but when your brain is going six million miles per minute at 1:00 am is damn hard. Other friends said, “Trust your instincts – if you think something is wrong, you’re probably right.” Except my instinct is broken (thanks, past jerky guys I didn’t leave sooner) – on days when I felt all calamitous and doomsday nothing could be said to make me feel better.Then I’d wake up in the morning and be all shameful in my head. “Hmmm, it appears I overreacted. Good thing I didn’t say anything.”

Never mind that he’s never truly given me a reason to doubt how he feels. I knew I couldn’t go on feeling so uncertain or else I’d end up inadvertently sabotaging the relationship and he WOULD leave me. So I did what I hadn’t done since I was going through my divorce and I high-tailed it to a therapist. Which I, perhaps, should have done before I started dating, but it was too late for that.

To be clear here, I didn’t go because I feel dependent on Greg or was looking for a way to save our relationship. Our relationship is awesome, but I needed to understand why *I* was causing all these problems in my head. I needed to save myself from myself.

I asked the therapist, “Why is this happening NOW? Why didn’t I feel this insecurity when I first started dating?”

Her answer? “Because now it matters.”

Ah, yes. Now Greg and I have been together seven months. Our kids have met each other and our lives are becoming more intertwined. We have more to lose if things fracture. Enter freak out mode.

Through this all, Greg has been incredibly patient. I try to keep most of my doubtful thoughts to myself but several times when I couldn’t contain them I’ve told him about my insecurities and he handled it better than I could have imagined. After being married to a man who’d get very angry any time I brought up something that even hinted that our relationship was less than 100% perfect, I can’t tell you how reassuring it is to have Greg open to, you know, using his speaking and listening skills to have conversations about our lives.

I’m not the only one dealing with the baggage of the past, either. Greg has been battle-scarred by his tumultuous interactions with his ex and seems to fear that I’m going to end up like her. While I know there’s no way I could ever, in a lifetime, think so many nasty thoughts as she fits into a day, Greg has a wariness about him that suggests he worries all women will eventually spout such meanness.

I take each day at a time. We’re both still learning about each other and learning to trust. As I mentioned, the kids have met each other and love getting together, which is awesome but adds another layer to the complicated puzzle. Now not only do I worry about how I’d feel if Greg and I broke up, but I have to worry about how my kids would feel, too.

I’m hoping, for both of us, that with repeated trustworthiness the insecurities will start to fade away and we can one day laugh about how scared we were to fall in love again.


P.S. I got my nose pierced in August.


Image used under creative commons license. Can’t seem to find the artist’s name, I’ll update when I locate it again.

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9 thoughts on “Dating and Insecurity (Plus an Overdue Update)

  1. I think this totally makes sense. . . that you would be scared and insecure now when the relationship has taken more serious turn by brining the kids into the picture. He seems really genuine, but of course you have to believe it! I’m thinking good thoughts for you two! And nose ring . . . WOW!!

    • Thank you for the good thoughts!

      Ha, it’s actually a teeny tiny stud, but yes, I did it! I’m not sure I’ll keep it forever, I feel like I’m going to hit an age where I feel it’s wildly inappropriate, or perhaps I’ll need to take it out when I go job hunting again, but for now I really like it!

  2. Kira,

    Nice to see an update and your experience with new found happiness.

    So thrilled to hear you finally got your long sought after nose piercing and tiny stud. Recall sharing my similar experiences of finally getting my nose pierced with you after my divorce. Hope some of my reassurance helped you gain the self-confidence in finally realizing your dream getting a teeny, tiny little nose stud.

    Promise you’ll love it as you grow older and be jealous of anyone who wants you to take it out. Your badge of honor has been hard fought with difficulties in marriage, divorce and reestablishing your personal self-esteem. Like any time I’ve changed my outward appearance, I thought I might look different, but I’m still the same old me. I didn’t sprout dreadlocks or suddenly become exotic. I still look like a milkmaid without the pigtails, only now I have a stud in my nose. The truth is I changed (A little. Maybe. We’ll see.) and the new bling is just an expression of that, and a physical memory of this trip. Every time I look in the mirror, every time I smile when someone compliments me on how cute my nose stud looks. I’ll remember this trip. And that sometimes the best thing you can do is exhale. Through your mouth, just in case.

    For all of us who shared your journey to happiness, please share a picture of yourself with your nose piercing because we know you’ll be smiling 🙂


    P.S. If worried about sharing on your blog, then please send me a e-mail. I know you’ll look super cute with a little sparkle in your nose.

  3. Oh my, yes to all of this! I just found your blog through The Happy Hausfrau. My BF just moved in with me and my children, and NOW I’m over-analyzing EVERY move, text message, kiss. The advice from your therapist is spot-on. Thanks for sharing!

  4. Kira! I’m so glad I found you through The Happy Hausfrau because I am in the throes of dating and laughed when I read your post about “just break up with me already” as I’m getting ready to end things with a guy who told me last night he was still in love with his wife — who passed away 18 months ago. Ugh. Things I never thought I’d hear said to me. So happy you’ve found your way to a nice relationship and love knowing I’m not alone in all this grown up dating …

    • Hello, so happy you stopped by! Yeah, dating with kids/exes is completely foreign, in that it looks nothing like dating pre-babies/-husbands. Sorry to hear you’ll be ending things with your current interest, but that will open up the door for someone who is ready for you.

  5. Pingback: I’m Still Here | A State of Motion

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