On Dating, Intuition and Being Brave



One of my favourite parts of my job is when readers email me with questions. I don’t always feel qualified to answer them (after all, I always joke that this blog is basically the blind leading the blind – except when it comes to sex toys. I actually know quite a bit about those.) However, the email below, which was sent to me by a reader that I also consider a friend, hit really close to home. It was one of those, “Yup. Girl, I have been there” moments. Because of this, I thought it would be a really good one to answer on the blog –

“Simone – I can’t bring myself to date yet! How do you bounce back from all the whack situations and disappointments? What is your mindset when you date? How do you know when to walk away? I feel like I’ve lost faith and trust in myself for misjudging the last two situations…I always try to make things work or give it more time “to see.”

 I also have this belief that my anxiety and any flaw in me has to be fixed before I can truly attract the love I want and be the partner that I envision. This is a really good mind trick to never date again! In short: gearing up to get back out there but terrified.” 

Ok, so a few things –

First of all, if you’re not ready to date – that’s totally OK. I feel like we live in a culture where everyone is constantly being encouraged to date, pair off and be together – something that just isn’t always realistic, fair or even healthy. We’re fed the message that if we’re not dating, in a relationship or trying to find one, that there’s something wrong with us – something that inevitably needs fixing. This couldn’t be further from the truth. Sometimes hearts just need time to heal. Being alone can help facilitate this. If not dating feels like the most authentic and right thing for you right now; follow your intuition. However long you need, there’s absolutely nothing wrong with taking a breather.

The truth is, although this blog covers a lot of my life, there are also a lot of things that you don’t see. It may seem like I’m always dating up a storm; immediately climbing back atop of the proverbial horse every time I get knocked down, however this isn’t always the case. Over the past three years I’ve taken several lengthly hiatuses from dating and sex. It just doesn’t always read this way because more often than not, I don’t always write about my experiences in real time.

With that said, this wasn’t always the case. While writing my book, which involved digging through the romantic wreckage of my past, I realized there were so many times that I flung myself, head-first into various relationships with very little regard for my own self-preservation. I practiced what I like to call “emotional cliff-diving.” I wanted to feel and experience things, and didn’t really think through consequences. I was brave to a fault. I had some good experiences but also lots of really, really bad ones.

Although a lot of good writing material came from these experiences, I wouldn’t recommend emotional cliff diving to anyone (well, at least anyone over the age of 23.) With that said, here’s what I’ve learned now that I’m older and a tiny bit wiser: dating is always going to make you feel somewhat vulnerable. The only way you can avoid vulnerability is by closing yourself off emotionally from other people – which doesn’t work if your goal is to meet someone. You have to be brave. Once I decided that I wanted to start dating again, I realized that the only way I was going to get through it was by becoming comfortable with the uncomfortable. 

If you do get knocked down, give yourself time to heal and then get back up again. Don’t dwell. You’ll get there. Be brave. Screen Shot 2015-06-04 at 12.42.45 PMWhen it comes to walking away from relationships, it may also seem like this comes really easy to me. It doesn’t. Throughout my dating career I’ve struggled with letting go of people, even when I know the situation is no longer a good fit. However, I’m getting better at this. My best advice would be this: always trust your intuition. Your gut gives you better dating advice than any “dating guru” or I can.

I’ve discovered that dating involves finding a healthy balance between being open (giving things a chance) and following your intuition. It’s important to remain open to new experiences, however if a situation doesn’t feel joyful or feels “off” to you – trust that. I used to think that I needed a specific reason to break up with someone (for example, they had to be or do something horrible) however, just because someone is a good person, doesn’t mean they’re the right person for you. As one of my favourite authors, Cheryl Strayed says, “wanting to leave is reason enough.” Your time is precious. Give yourself permission to walk away from things that don’t feel good. 

Lastly, there is nothing about you that needs fixing. You are perfect just the way you are. We all have our “stuff.” Take it from me – I live with an anxiety disorder and although it’s mostly under control thanks to medication I take everyday, sometimes it can still make me feel a bit wigged out. I’m also a 30-something who lives with their mother, writes about sex on the internet and spends a lot of time playing with dolls. On paper, I’m sure there are a lot of people who would say, “I’m going to stay far, far away from that one” – or at least that’s what I used to think.

What’s different about how I approach dating now, versus in my twenties, is that my attitude is a lot more “take me or leave me.” I made the decision a few years ago to stop allowing myself to feel insecure about the things I mentioned above. Instead of always trying to bend to what I think people expect of me, I just decided, for better or worse, to own the hell out of who I am – weird dolls, sex toys, anxiety and all. I know I’m not for everyone and that’s OK. I’m not looking to meet and fall in love with everyone – just one person.

The funny thing is, this new approach has actually worked. I now have guys tell me things like, “you’re so confident…it’s almost intimidating.” However, I don’t know if it’s confidence so much as I just got tired of being let down after putting time and energy into people who never really accepted who I was in the first place.

We’re all works in progress. We all have our weaknesses, flaws & quirks. Instead of focusing on what you think needs “fixing” turn your attention to the things you really like about yourself – the things that make you feel awesome. Do more of these things. Be loud. Don’t cower.

The right person will accept all of you. I promise.

Sending lots of hugs from me and encouraging fist bumps from Joe the Intern,



If you’d like to see more posts like this or have a question of your own, please leave a comment or get in touch. I’d love to hear from you! The image at the top of the post is by Joe Webb

  • Alana Margaret

    I love the advice about the “take me or leave me” approach. I met my husband on OkCupid and so people are always saying “OH! So it works! Did you like it?”. My husband and I both hated being on OkCupid and it worked for us because we had both gotten to the point where we weren’t invested in making ourselves likeable. I stopped treating dates like I was the interviewee, answering every question correctly to get a second round and instead put myself in the position of the interviewer, “Do I really like this person? Do I actually care if they like me?”. I started going on a lot less second and third dates that I knew in my heart were going nowhere.

    • skinny_dip


      My dating life also got better when I stopped caring so much about what other people thought & instead asked myself, “does this feel good?” + “is this a good use of my time?”

      That’s awesome how you & your husband met!

      • Vanessa

        Okay so let’s say you go on a date and you assess and decide it feels good and is worth your time but the guy bounces (silently or directly)? It still astounds me how we can feel palpable feelings that are not in fact returned…What do you tell yourself about your judgement then? It almost feels like whenever my internal voice says YES the dating situation implodes and only when I’m lukewarm and could care less genuinely about going further, do things sort of work out (for a period of time).

        • skinny_dip

          Ok, so first of all – I’ve so been there. I can’t count how many times that I’ve gone out with someone and thought “this could be it” only to have it blow up in my face. Unfortunately I think this is just the way dating goes. You have to take risks and be open, even though there are no guarantees. In my experience, you just have to just stay open and eventually you’ll attract the right person who will be worthy of your time & won’t bounce. Learning to trust your intuition is an ongoing process.
          You could also ask yourself what went wrong with these situations and what went right? What did you learn? Use your answers to guide you in your future. Good luck! xoxoxo

  • Ria

    The timing of this post couldn’t be better. I actually did the mistake to apologise for being the way I am, and showing it (including being sensitive and having anxiety), and got the advice to “pretend” from a certain guy. I was also called defective from another guy due to a surgery scar (both within the last 3 months). In both cases my intuition/instinct was facepalming all the way. Thing is, I can’t change who I am. And to be honest I like it. And so do the people who love me, and who actually have taken the time to know me. So, taking what you say into account, I think I’ll start treating myself the way I want to be treated (including dates for one to places I wanted to go, but were too “silly” for dudes of the past), and get to know me and love every part of me so well, that I’ll stop giving me away, when I know I’m worth so much more than that.

    • skinny_dip

      “I can’t change who I am. And to be honest I like it. And so do the people who love me, and who actually have taken the time to know me.” – YES, YES, YES to all of this!!

      FYI, You should definitely take yourself on some awesome solo dates 🙂

  • I really needed to read this today. I know it wasn’t meant for me but it kind of feels like it was. <3

    • skinny_dip

      It was meant for everyone! <3 Glad it resonated with you, dear. xox