Date #2 with The Teacher

Duration: 7 hours (which is like 2 hours in drunk time)

Where: Restaurant/Piano bar

Key points: I got drunk. We sang. He definitely wanted us to go home together. Instead, we made out in his car a little bit. To steal dateadreg’s word for it… I want him in the slow lane.

We were supposed to have dinner, but I was not hungry, so we munched on a few apps and chatted. He was asking me a lot of odd questions, such as: “Where do you see yourself in five years? Who, alive or dead, is the one person you wish you could meet?” etc…  I thought it was strange, but I think he was doing it to try to prevent conversation lulls. (I can be painfully shy/ socially awkward.) I think his questions were actually making that worse. After I got him to knock that off, things were better. I felt he was a little rude to our waitress. She was a bit of a ditz. He was being sarcastic towards her dumb questions. I think he was trying to be funny, but with one look at her face, it was obvious that she was not getting it. I told him to be nice. He appreciated my upfront attitude.

He heard me sing (which is reserved for my poor neighbors while I am in the shower). He was impressed with the amount of song lyrics I know (owlie’s only bar trick…).  I think he picked a good activity for us.

When we left, it was 1 or so… and he said, “where to?” Then he mentioned how close we were to his place and suggested we go there. I asked him coyly, “to do what? hangout with your roommates?” He backed down pretty quick after that. He said he wasn’t ready to go home yet, so we went to another bar in my neighborhood. He made some comment in passing that I could invite him back to my place. Nope. Nope. Nope.

He pulled up to my building, we made out a little bit, and then I retired to my nest alone.

We shall see what happens next!

With the girl whose messaged spurred on me making that post, I felt like I was doing all the work in our conversations, and she had to cancel on me a couple of times. And my feeling about cancelations is that whoever did the cancelling should set up the next date. And I don’t want to be that guy always texting and coming off and being too keen/ creepy. Which is just as bad.

The end...or is it?

Following on from my previous post, and while I will be discontinuing to make posts to this blog, I’ve made a decision on what I’m going to do next and I’ve now done 2 things:

I have opened up this blog to now receive posts, which again can be submitted from here:, if there are others out there who wish to share their experiences with dregs and/or their dating woes, and if there’s a want to keep this alive as a share point. I will be playing editor though, so will provide feedback if there’s anything unsuitable being submitted! 

The other thing I have done is I’ve created a new blog, which for those who wish to continue following my updates and journey into more relationship type stuff, as opposed to dating, you can find me here:

I’ll be taking my time initially to work out how I am going to evolve my blogging, so do bare with me as I adapt to a new style and perspective. 

My posts on Tiger won’t share each and every intricate detail as I did with dating, but I’ll make a point of updating in a more general and topical sense. I guess I’ve developed a love and relationship with blogging as well!

Thank you to all my followers of dateadreg for being there at all those moments of anguish and hilarity. It made it all worth my while and I appreciated all the comments and wisdom that had been given to me along the way.

Not quite a good bye, but it is the end of an era. In closing dateadreg, I will say this:


There is an element of monotony involved in dating that will send you to a place on the odd occasion where you just can’t take it anymore. You just have to persevere. Take it on as a challenge - something you want to become a pro at. Learn from each and every experience, and let it drive you for improving on the next one. Always be the bigger person that takes charge and calls the shots - and always let go when it’s not working, no matter how hard that is. Put yourself first and foremost. Learn to be happy with it being just you. Stay busy - dating is not the one hobby to have! Though dating in itself can keep you busy.

Date as many men as you can in the beginning. Options are the key to narrowing down. And if they all don’t work out, just go back to the drawing board and start again! (hence monotony) Juggling men can actually be fun though and makes you feel like the powerful woman you are!

And when you find a good one? Don’t play games, just let it flow naturally and try to keep your head. Ride the storm of “what is this?” and see where you come out the other end. 

Always approach with caution. Don’t jump in too quickly. Don’t trust too quickly - let him SHOW you the type of guy he is.

Categorize men into one of two categories: slow lane or fast lane.

Slow lane guys are the relationship potential men - the ones you don’t sleep with on a first date. The ones you slowly build rapport with and get to know. The ones you feel either could grown on you, or straight away give you a wow factor. They need to be ticking a lot of boxes to be placed here!

Fast lane guys are those obvious men who aren’t after commitment, but you’re physically attracted to. They’re always good for a bit of short term fun - but make sure you’re in control and limit it. There’s got to be something about them that makes it easy to decide that you don’t want anything more - something small that puts you off.

Have a period of time in your mind that’s a ‘testing the waters’ period - like probation. You need to know for sure that person is someone you want to be with longer term - who isn’t going to surprise and shock you with poor behaviour that leaves you hurt and confused. Remember, some men are better than others at hiding their inner arsehole, so moving at lightening speed into a relationship is just bad news.

But if a guy can prove it to you - that it’s OK and he won’t hurt you, then you have to let the walls down bit by bit - giving him more of you. It’s terrifying at first, but it gets easier. And just remember - he’s made it clear and OK for you to do this, so if he were to turn off the lights all of a sudden now - then that’s not you to blame, as he’s just a cruel person. The only thing to do then is to buy yourself a cheesecake and take some time out! Then try to get past your neurosis for the next one…and the next one…

And then all that’s left to learn is how to let the right one in… 

dateadreg x

Oh yeah, asking a person out is a first message shows that you are garage nightmare of a person. Even at my most Don Juanish, I’ve never done that. I have suggested to the person that we start a Ken Adams fan club, and the first rule should be “no pants.” In my defense, that totally worked.

So basically, I can stop feeling like a real creep for thinking the whole point of online dating is to get offline at some point?