lilbabe79:
Hi
I have this male friend I’ve known for almost 20 years. He courted me back in the days but I was not available so we remained friends so far. Life keeps pulling us apart and bringing us closer (geographically). He now lives on the other side of the world but we cal each other all the time. He’s my best friend, support and confident. He knows everything about me and I about him.
We talk a lot, laugh to the same things etc.

We stayed at each other’s place multiple times over the years, even sharing a bed now and there but he never tried anything

Now we are both 40 with a few failed relationships under our belt.
He keeps telling me how he wants to settle and start a family. We talk a lot about the fact that the best way to go is marry your best friend, someone you really know and so on.

I have this odd feeling that he’s trying to test the waters with me but he never says anything definitive

I’m really wondering if I should make the first move and tell him we should give it a try.
I’ve never done such thing in my life and I’m afraid he would say no. If he does, our friendship would probably take a hit.

What do you suggest ?

extremelygolden:
Go about it in a playful manner. In the middle of a conversation when he says something that thrills you, just chip in a sentence like, O!Jay I love you more each passing day. You make me happy always by your perception about life. If you were around now I would have said, what have you given me to eat? I am just loving you too much these days. Then you quickly change the topic.

You will see that after some time he will call to confirm if what you said about loving him is true? That's when you will tell him Yes in a bold letter.

Best of luck, dear.

lilbabe79:
Hi
I have this male friend I’ve known for almost 20 years. He courted me back in the days but I was not available so we remained friends so far. Life keeps pulling us apart and bringing us closer (geographically). He now lives on the other side of the world but we cal each other all the time. He’s my best friend, support and confident. He knows everything about me and I about him.
We talk a lot, laugh to the same things etc.

We stayed at each other’s place multiple times over the years, even sharing a bed now and there but he never tried anything

Now we are both 40 with a few failed relationships under our belt.
He keeps telling me how he wants to settle and start a family. We talk a lot about the fact that the best way to go is marry your best friend, someone you really know and so on.

I have this odd feeling that he’s trying to test the waters with me but he never says anything definitive

I’m really wondering if I should make the first move and tell him we should give it a try.
I’ve never done such thing in my life and I’m afraid he would say no. If he does, our friendship would probably take a hit.

What do you suggest ?

extremelygolden:
Go about it in a playful manner. In the middle of a conversation when he says something that thrills you, just chip in a sentence like, O!Jay I love you more each passing day. You make me happy always by your perception about life. If you were around now I would have said, what have you given me to eat? I am just loving you too much these days. Then you quickly change the topic.

You will see that after some time he will call to confirm if what you said about loving him is true? That's when you will tell him Yes in a bold letter.

Best of luck, dear.

extremelygolden:
Go about it in a playful manner. In the middle of a conversation when he says something that thrills you, just chip in a sentence like, O!Jay I love you more each passing day. You make me happy always by your perception about life. If you were around now I would have said, what have you given me to eat? I am just loving you too much these days. Then you quickly change the topic.

You will see that after some time he will call to confirm if what you said about loving him is true? That's when you will tell him Yes in a bold letter.

Best of luck, dear.

derrydinny:
don't go and toast him o, be asking us question


he decided not to woo you again after it didn't work out years back because of you, make amends grandma