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I have tried to psyche myself up, but no way can I do it... how do I ask him out???

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Question - (16 February 2010) 3 Answers - (Newest, 28 February 2010)
A female United Kingdom age 51-59, anonymous writes:

Further to a recent post..... I am going to take some of the good advice given and now want to ask the bloke I fancy out. We are friends, both mid 40s and have been friends for nearly a year. He tells me lots about his life and is a really private person so this is unusual. He has said that I am one of his closest friends but gut instinct says he likes me a bit more than just a friend. we are in contact one way or the other nearly every day. He emails me loads. He doesnt appear shy but he is and is also really lacking in confidence. He had difficulties at school with learning and other kids (undiagnosed dyslexia and dyspraxia)

He hasnt ever moved out from living with his parents and hasnt had a long term relationship - I dont know if he has had any relationship, he doesnt talk about any past girlfriend. He's not gay.

So big problem now - is how to do I ask him out? I absolutely cant just ask him out when talking to him - I have thought about it and tried to psych myself up, but no way can I do it.....

I have asked him out and hes asked me out- we always go just the 2 of us but it never goes beyond a hug at the end of the night. He even took me out to dinner and organised and paid for everything. Although he always texts me on the way home to say what a lovely evening he had and how good it was to see me.

So what do you guys think about me sending something by text. I know it seems a strange way to do it at my age but I have thought about it a lot and my reasons are as follows

Although we see each other often its usually at lunch when we have to go back to work afterwards. We often have a chat back and forth via text when we cant see each other.

He finds it difficult to talk sometimes about feelings etc and I dont want to put him on the spot and make him feel embarrased.

Any advice would be gratefully received.... thanks xx

View related questions: confidence, moved out, shy, text

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A reader, anonymous, writes (28 February 2010):

you could find out what he likes or a movie he is interested in seeing? get tickets, offer him one! the worst he could say is no thanks, right? go on and take a chance, either way you win, he says yes? you're golden, he says no? you are still a strong confident woman in charge of her life!!!

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A reader, anonymous, writes (18 February 2010):

This is verified as being by the original poster of the question

Thanks so much to both of you for taking the time to reply. I'll let you know if I have any luck....x

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A female reader, anonymous, writes (17 February 2010):

You know him so yes... why not send a text its perfectly acceptable form of communication and the fact it is a little different to your normal way will make him realise you are feeling different too. I think if you really want this relationship to move up a gear though you need to be open about your true feelings at some point soon. Think carefully about his living arrangements. He sounds like a polite and caring man but you clearly need a relationship to meet your needs too - its time to see if you can both develop things further. You have nothing to lose!

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