Posted in Dating / Relationships

How Dating Built my Confidence for Dating

I’d said in the past that my relationship history was pretty woeful. My ex-wife was my first and so far only relationship. The only person I had dated until that point. I’d spent most of my life feeling like a fish out of water where women were concerned. Shitty experiences during my teenage years were dredged up as part of my therapy.

Naturally then, the prospect of dating, approaching and meeting new people was one of the most terrifying things I would ever do as part of my new life. I expected the worst; I truly believed that I would not get a single date no matter how genuine or approachable I was.

But why?

I don’t fit the “tall dark and handsome” conventions. Nor am I muscular, rich or successful. I’ve had just one relationship, a single sexual partner whom (in my mind) did not want me touching her (so must have found me repulsive). I had a broken marriage with a person who said it was my fault that she cheated. So my assumption was that any woman would judge me as too weird and broken to be worth the bother – and would see that there was something seriously wrong with me… after all, everybody else could.

These were not just a reasonable assumptions to make, they were incontrovertible facts. I was destined – in my mid 30s – to spend the rest of my life single. This was also the issue that Fennell’s book could not help with. Applying the tools in her book, tools that had worked on my other self-esteem issues, not only failed to work but actually made me feel worse. I had no previous experiences to draw on with which to challenge these negative self-perceptions.

So I did the only thing I could do: I joined a dating site and went in with an open mind. I treated it like an experiment – prepared for the worst but hoping for the best. I expected to receive one response for every 20 messages I might send. I was prepared for unrealistic expectations from women on there (lists of demands that any potential partner must be – I don’t see many of these but they are there). Most of all I was prepared for the rejections that I had come to expect in life.

I was on OKCupid for three days before I got talking to Little Red. We talked about a lot of stuff and when I finally came to ask her out on a date… my chest pounded. This was the most terrifying thing I had done in a long time and it took only a short sentence. “We’ve got a lot to talk about still so how would you like to meet for a coffee this weekend?”

Making that approach can be quite terrifying… but “fortune favours the brave”

F*ck! Did I just ask her that? OMG! I just asked this gorgeous, funny, intelligent, successful woman out on a date. What did you go and do something like that for?
She’s going to say no… isn’t she? Of course she is…
Err, what do you mean “Is Sunday morning ok for you? Costa, sure! Let’s keep it simple. Ok, see you at 11! Have a good evening 🙂 Haha! don’t be nervous… no, I haven’t done anything like this before either.”
What the hell just happened? Errr, looks as if I have a date for Sunday…

I was terrified waiting for her. My pulse was still going crazy when I saw this beautiful, petite redhead come toward me in the rain, a look of uncertainty flickering across her face. I know that look now. It means “Is that him? I think so…” So anyway, I was nervous but at no point did I show it. I stood, asked her name… she nodded. I leaned forward, put my hand on the small of her back and kissed her on the cheek.

Sheeesshhh… I can’t believe I just did that either!

We relaxed and my nerves dissipated as I settled into enjoying good company and good coffee. With each successive date I remained nervous, and I still had the hang ups about the girl disappearing at some point or texting a friend about how rubbish a time she was having. No date bolted on me. The more I did it, the more relaxed I became about doing it. The more relaxed I became, the bolder I was about asking to meet again and generally making the first approach on a dating site. I would never be that nervous again until my first date with ubergeek and that was purely because of how promising it already was at that point.

Though I was not ready for a relationship, meeting somebody with all the qualities I desire in a partner began that slow process of tearing down the walls of poor self-esteem… and this person not only wanted to meet me once, but twice and a third time. It was the biggest challenge – no the only thing that challenged my dating hang-ups. I could no longer cling on to the notion that I was so unappealing, so boring, so weird, so… ugly that no woman in her right mind would ever want a first date with me, let alone a second, third or heaven forbid… something permanent.

Working through Russ Harris’ book The Confidence Gap, I have already discussed that he states that we must display confidence before we feel it. And looking back, that is exactly what I did on my first coffee date with Little Red. I was terrified – I had no idea what to expect and I was already convinced that she 1) was out of my league 2) would not want to see me again. But she did – and we did meet again. My confidence also grew in realising how much courage it took to ask for the date. Most people get nervous here but for me, it was at the time a remarkable achievement.

So if you are nervous about going on a date and have serious self-confidence issues, the best thing for you to do is put yourself out there. There are many fish in the sea and sooner or later, one will bite. Be prepared for a lot of rejections. Be prepared for a lot of unanswered emails. Be prepared that they might be different online and in real life. But… also be prepared to meet some wonderful people on the way.



I go by the name of Frank Speaking. My blog "In the Mind of Men" (former name Chin Up, Chest High) started out as a chronicle of my mental health recovery. Now it is a forum where I discuss issues related to male mental health.

2 thoughts on “How Dating Built my Confidence for Dating

  1. I’m so glad you shared this. I never thought about the guys’ persepective on the date and how they may deal with nervousness.
    I’m also glad that you are out of that marriage and are free to find a woman better suited for you and am building the mindset to get it!

    1. Beneath all the cock-suredness of it all, we’re just as nervous as you are. Funny thing is, men and women always assume that the other is less nervous than they are because of how confident we all try to appear on the outside on a date.

      I think we’d all do ourselves a service to remember that though you’re nervous, your date is likely to be just as nervous too. Maybe we’d all go easier on ourselves in the dating game.

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