I am female and I have a guy who is my best friend for 3 years, whom I have fallen for. We hang out together all the time. We are in our 40's. We have never shared intimacy but lots of flirting & lots of chemistry. We do things together all the time. I would like to ask him about changing the friendship to a relationship. I need some help in choosing the right words and approach. He is taking me out to dinner this week for a post New Year's celebration. I want to know as we start this new year so I can either go forward with him or move on.

Here is some of what I was thinking please tell me what you think & offer advice & suggestions.
When to say it??
1. approaching the subject at the end of the night once we are saying goodnight in the car so if he says "no" it does not make the whole evening awkard

2. inviting him up at the end of the evening and saying it once we are inside
(hopefully he'll come up but I need an alternative if he does not)

3. saying it at the end of the dinner (but if he says "no" the drive home may be awkard).

What to say??
1. we have a great friemdship and I would like to take it to another level and wanted to know what you think? I would like us to date as a couple?

2. What do you think about changing this relationship & dating?

3. I really enjoy being with you, I respect & appreciate who you are as a person and I miss you when I'm not around you. I'd like to take out friendship to the next level & date. How do you feel about that?

I know he has been hurt a couple of times & is a bit shy.
Suggestions, opinions, please!!

Call him right now and just tell him you love him and wait and see what he says.:cool:

I don't want to scare him off. Seems like that would really scare him off.

If he feels the same way you do I doubt it!:cool: Seems to me you guys are already dating!:eek:

Well it's like we are dating.. but we are not. We do a lot of thing togthere but there has been no intimacy.

If neither of you is seeing anyone else then you are dating intimate or not!:cool::eek:

Well I still think I have to raise the issue and see what response I get so I know for sure where this can go.

Anything worth having is worth taking a risk for,I wish you luck and I'll keep my fingers crossed for you!:cool:

Thanks talaniman.
So do you have any suggestions re the "when & how" on my original question?
Are you male or female?
If you are male what would get your response the most?
If you are feamale which would you do?

Hi I think you should just be yourself and at dinner near the end just say too him.

Ill have my fingers crossed for you

I am a soon to be 52 year old male married w/children? For the last 30 years.If I read you right for the last 3 years you and this felloe have been going out and are pretty good friends so you can't say that an admission of love would come as a surprise!You say he's shy I don't know but the way I see it is one of you can make a move or just keep things like they are.Just grab his hand clear out the blue say I LOVE YOU... then see how he reacts.If he runs like a scalded dog,you have your answer,IF he says it back... intimacy? Well you get my drift just throw it on him and stand back.. no flowers, champaign, or a lexus.(handcuffs up to you):cool:

:) actually he drives a Lexus

I agree with both these guys. Just be yourself and just tell the guy how you feel. Don't wait too long to tell him.

Ok everyone the deal is I do plan to tell him. Without question.
My original question was "how to say it" and "when" all based on our planned dinner date this week.

I suspect you are the scared one here.and I've answered the how(just say it) and when(asap) the rest is up to you!Good luck!:cool:

No actually I am not scared I just want to know. So I can either move on with him or someone else.

You've known him for 3 years and you obviously know him pretty well, so you probably know what to do or say better than any of us on this forum could advise you. I'm sure you've had time to "feel him out" and can probably predict fairly well how he'd react if you were to approach the subject with him. Actually, you might want to try it "without words" first, if that makes any sense to you. What I mean by that is encourage him to be a little more affectionate and romantic towards you. You do this by behaving that way towards him. For example, hold his hand, hold his arm as you walk out of the car into a restaurant or wherever. Kiss him not only goodnight but whenever the mood is appropriate. Even if he doesn't initiate these things with you, do it with him. If he responds in a positive manner, then you have your answer. Now, if the two of you already do these things on a regular basis, then I'm sure he's just as open to the idea as you are and you likewise have your answer. Then you can apporach the subject with him and in all likelihood get a favorable response.

Yes I agree with everyone, just tell him how you feel. I don't think he will be scared away, because you two have known each other for quite a while.

I am a very direct person, but... I think if it was me I would simply say, I have something really important to tell you... and then just say how I felt. Short and sweet and to the point. If he's at all attracted to you he'll be flattered and excited. Good luck!

I simply called my good friend (now wife) and asked if she wanted to go on a real date with me. Her response was "you know that will change our relationship". I agreed and told her I had given it thought. She asked for an hour to ponder it. That was several years, one child and now a grandchild ago.

The worst thing you could do, In my opinion, is denying your feelings, only to wonder "what if". If he is not romantically interested, but truly a friend, it should be no harm - no foul situation. If he is interested... remember us guys like flowers, too. ;)

Good luck.

Edited for spelling

Citylover, I'm also a city girl. If you really like the guy, you shouldn't be embarrassed to show it. Don't be afraid let him know how you feel about him. Ask him out to dinner and if you get tongue tied during the date, talk about your job, what's going well or if you have a hobby talk about that. After dinner invite him in so you can talk to him in private. If you don't know how to ask him in, say, Would you like to come in for a cup of coffee or a drink? Once your alone with him and your confident, let him know how you feel about him. He probably likes you too, but doesn't know how to impress his feelings. I think he will be flattered to know that you like him. Hopefully, he will say the same back to you. Good luck.