Posted in Dating / Relationships, Self Esteem

The Thoughts in Your Head on a Date When You Have Self-Esteem Issues

I can hardly believe it’s been over three years since I last went on a date (not a bad thing, I’m in a relationship as my long-term readers will know). At the time I started dating in late 2012, I was also starting to do something about my self-esteem issues. That meant much more anxiety than anybody else may be experiencing. I remember most of my dates with fondness. Equally, I remember some of the critically negative thoughts that accompanied even the best dates.


Why is She Texting?

There are always natural breaks in a date. The most common would be for toilet breaks or to order a new round of drinks. Whenever this happened and it was my turn to order or it was at the start of the date and I offered to get the first round of coffees, I would naturally turn to look at my date. Nearly always I would see her on her phone. Panic would set in. Why is she texting? Is she texting a friend to tell her she’s having an awful time? Is she telling him or her that she can’t wait to get away? Is she listing my faults? Is she telling her friend I am far uglier than my photos suggest? When you have low self-esteem, you default to the negative. It doesn’t even cross your mind that she might just be texting a friend about something unrelated. It never crosses your mind that she may be confirming she’s safe and you are not an axe murderer. It never crosses your mind that she might actually be describing you as “lovely”, “charming”, “funny” or “interesting.”

Will She Be There When I Get Back?

You will need to toilet and that means she is out of your sight for a few minutes. That means anxiety about how long the date will go on. Will she still be there when you get back? When you’re convinced that you’re too ugly, inadequate, not good enough and that there is so much wrong with you that she would never be interested in you in a million years, you prepare yourself for it. In a way, it’s actually quite comforting in a twisted sort of a way to expect her to bolt during your brief absence. Again, even when the evidence suggests otherwise, you still expect her not to be at the table when you get back, her full cup of coffee left all alone on your return without so much as a goodbye note.

It’s Only a Matter of Time Before She Realises

This is a thought you will get on dates but away from them too. When she texts you to let you know when she’s available, when she contacts you to ask you out to dinner, what sort of day you’ve had or even just a joke for a Monday morning and she’s “wondering how you’re doing today” (yep, I got a few of those), in your mind, it’s only a matter of time before she realises that you’re a pointless waste of time. It’s only a matter of time before she realises she can do better. You’re wondering all the time when she’s going to ask herself the question “what the hell am I doing dating him?!” Ultimately, your natural instinct is that she’s settling for dating you until she can get a better offer.


Low Self-Esteem is Difficult to Overcome

I went through all of that and more. It’s hard to look back now and not see a bag of nerves when I first started dating even though on reflection I took to it like a duck to water. I was put at ease very quickly when I had a couple of wonderful dates with Little Red and 95% positive experiences from the process. That’s not to say I got over these very real fears quickly; I didn’t. They were there even during and after therapy. Some of my dates to whom I later confided these negative feelings expressed surprise, saying I came across as chatty and open and put them at ease quite easily.

I’m still in contact with three of my dates (Miss Outdoors, Little Red, Bookworm) and was recently surprised to receive a Facebook friend request from a fourth – Indiechick. She was other the option I had when I first started dating my girlfriend (who I referred to at the time as Mirror Image). In fact, it was Indiechick’s previous interest (and Mirror Image’s jealousy at that) that proved the catalyst for the early stages of our relationship.

When I look back now, it’s as though I am looking at a different person. Sometimes, I can’t believe I never thought for one minute that I would be able to attract the sort of women that I wanted to date. I was concerned I would settle for somebody who was not what I wanted just for some female company and attention. But therapy, time and experience taught me otherwise. I met some amazing, awesome, wonderful and gorgeous women – something that surprised me every time I received a positive response to a request to meet for a date.

I don’t really have any words of wisdom to impart for men with low self-esteem entering the dating market other than it is a mental illness and you should seek professional help if you need it.



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.

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