Shy Men

It is really difficult to put men into boxes like that. All of us are different and even shy men are individuals. That being said... there are a couple of ways that you can make it easier.

1. You could take initiative yourself. There is nothing wrong with suggesting you go out for coffee or a drink. I certainly wouldn't have a problem with this.

2. If you don't want to just take the direct route, you can provide a really clear safe path for you to take. Pick something that you would like to do that you know he would be OK with and is reasonable (i.e. not out of his budget or comfort zone). Then you just make it very clear that you would love to be asked to do this.

A woman I have been flirting with recently did this with me. I am not shy, and this wasn't necessary... but I didn't mind, it was a natural extension of our flirting relationship and it did make the road to an enjoyable evening really easy. It also was a clear way for her to communicate her interest in spending time.

Personally, I prefer the direct approach. I have heard that woman are counseled against taking initiative... but I personally don't understand this. A relationship should be a mutual thing.

But then, of course, every person is different and every relationship is different.

See your other post . . .

Shy guys may take an eternity to make the move.

I say, if the feeling is mutual, help him along, and he'll only get more comfortable.

And guys are forever trying to walk a tightrope between being too pushy and too wimpy.
With one woman I was being the perfect gentleman but we later split and she told me "You should have been more assertive" (whatever that means).
Yet another woman told me I was being too "pushy", so you just can't win..

When I was 22, I got to know a fabulous seeming girl called Mary at an art-student pub in Bristol* where I was a regular; we had mutual friends, we got on really well, we usually sat together. I had a strong feeling we could have a relationship. She invited me to have tea and toasted tea-cakes (and a joint or two) at her flat (well, bedsit really) in Clifton one Saturday afternoon. Although I generally got on well with girls and had had plenty of dates, I had been told before by a couple of girls I was too pushy and tried to go too far, too fast, so I thought "I'll play this gently". After the teacakes I was leaving and I said "Let's go out for a date" or words to that effect. She put on a kind of consoling voice and said "I'm sorry, I don't think so - I'd rather we were just friends."

I was devastated! For one thing, my strong intuition about it had turned out to be false which made me feel kind of lost, like my compass had broken. Also I was disappointed but I eventually got over it. The idea that if a girl said "No" she meant "No" seemed the respectful thing to assume. I changed pubs. About 2 years later I met the woman who was to become my first wife and one evening we both went to a club in Bristol (the Dug-Out of fond memory) and we ended up apart, talking to different groups of friends (there were 2 bars in the place). I was in the other bar, and guess who should appear but Mary! She seemed very pleased to see me and bought me a drink. We were chatting by the bar and she said "You know, I really fancied you a couple of years ago. What happened?". I said "But I asked you out and you said "No"! She said: "I just wanted to see how hard you'd try."

I immediately turned on my heel and walked away, leaving the pint of cider untouched. I was so cross! I told my soon-to-be wife about it and she laughed and said "You're angry with yourself, not her, because you now realise how close you were." I didn't think that was accurate. I realised what a narrow escape I had had. If she was the kind of girl who made men beg (so to speak) for a date, how many more hoops would she have created for me to jump through once we were an item?

Looking back I must say that this was one of the experiences in my life which helped me develop my own views about what kind of relationship I wanted and what sort of person I wanted to be with. The first wife thing didn't work out, but for different reasons!

I am with someone now. We met at a Halloween party in 1993 and went home together afterwards and have not been apart for over 20 years.

*The Adam and Eve, if you're reading this, Mary.

I guess he wasn't really shy after all. Maybe he just wasn't that into me. He suddenly stopped communicating via text messaging out of now where. I text him an open ended message when I hadn't hear from in a day. He never replied. The following dayI thought"Well, maybe he lost his phone or something" trying to remain optimistic so I decided to message him one last time although at that point I was a little suspicious that he was blowing me off. He never replied. It has been three days. He either lost interest in me or wasn't really interested in me to begin with. Thoughts?

Dear Contrex,
Wow! What an interesting story. Funny I kind a go through the same thing. I'm always afraid of coming on too pushy to guys so lately I've been very passive and because of this I think that I have been attracting men into my life that I am clearly not compatible with although they seem to think we are ....I know we are not because I know my real self. Im thinking the best advice here from what I have read in your article and my observations about my self is to just be ourselves....
Recently, I met a man that I'm pretty sure we would have been very compatible. Very. However because of being in a mode of passivity that I have grown accustomed to when I met him I wanted to be my self ...dance...laugh...scream but held back! Boy do I regret that. Lesson learned.

I don't understand why you are trying to mold yourself into a prize.

I wish you would be molding yourself into figuring out who you are - not what guy might like you.

Some interesting man might like you as you.

Good for you mate, all men hate that sort of women who play silly mind games!
Pity about the cider though...

I was very shy when I was younger, but still managed to initiate and conclude in under thirty seconds on quite a few occasions.

I am really glad that you tried. Sorry that this one didn't respond, but keep out there. We have all been on both sides of this... it happens.

You did the right thing.