Dating: Where do I even begin!!!

Dating is a complex thing, it is something that poses a million questions, oh and one other thing, it is something I have never done. I am 25 years old, and have never had a single date in my life, whilst I have had serious relationships, and I have had different sexual partners, I have never actually taken any of them on a date (which might explain my current single status). I am at a stage now where I am trying to work out whether to date or not, but I have a million different things in my head, such as what is a date, what am I meant to do, where would I take someone, how would I ask them, what do you talk about, with all of these questions, I am not sure that dating is right for me.

So let’s try and work out problem one, what is a date? It is hard to answer this question, because to different people it means different things, which is why it is a problem meeting someone for a date. She may think it is something different to what I think, for example, is this an interview of some kind to decide if we are going to see one another again. If it’s an interview, then I am nervous, I have to be careful on my topics of discussion, try and make them laugh, and try and be charming, none of which are my strongest points, my sense of humour is dry, my charm is nonexistent, and my topics of discussion would range from football to films, none of which I expect a nice young lady wants to hear about. Then there is the chance that this could just be a drink, an idea that I am far more comfortable with, I can happily sit there with a beer, and have a drink with someone, indulge in conversation, and just have a laugh with someone in the pub, that’s more my comfort zone.

Then there is the idea of what to wear, how do I even begin to know what to wear. I don’t want to over-dress, but I don’t want her to make the effort and then I look like I have just finished a shift on a builders yard. It’s hardly likely to impress. The ideal solution is to meet in the middle and go smart casual, but honestly, there is no such thing, for me, it’s one or the other, I am not the kind of guy that likes to wear his suit jacket with a pair of jeans, it’s not something that suits me, so I am almost always likely to wear my jeans, a shirt, and a pair of shoes, and then pray that I don’t look to under or over dressed.

Then there is making someone laugh, this is beyond out of my comfort zone. I can happily make someone laugh, but I don’t think they would be jokes appropriate for a date, I think they would probably be suited to a back street pub, where my gran and grandad went in the 80’s, so what do I talk about, and how do I make her laugh. I am not the most charming person, most of my humour comes from making jokes about myself or other people, and I hardly think poking fun at a girl on a date is going to make her want to meet me again. My thinking is that I just have to keep my jokes to a minimum, and hope that my conversation skills can help me (although that’s hopeful).

Then there is one final thing, where do I take them? If I take a girl to the cinema, I am almost certainly not going to talk to them, mainly because I hate people that talk through films, and if she did that, she would have a long walk home, and I would expect her to do the same to me if I did it. If I take her for a drink, I look like I am not really making the effort, a quick pint and a pack of Walkers is hardly charming (although well within my comfort zone). If I take them for dinner, am I not moving a little too quick, surely getting to know someone in a more comfortable atmosphere is better than whisking them off for a meal, and painfully watching them try and eat spaghetti without getting it on their clothes?

Previously I have just got with girls I already know a little about, dating wasn’t needed (well it probably was as I am no longer with them) so I used to get a little drunk, one thing would lead to another, and I would end up in a relationship, wooing someone is something I have never been good with, and with this much effort, I question if I will ever be good at it, but I think it’s worth one crack, so I shall let you know if I ever decide to ask someone on a date (which is another issue on its own) until then….. Wish me luck!


Sean Bromley


  1. Become Mr. Right says:

    Thanks for the great post!