Do I ask him out?

[Turtletea]

What should I do? My son's best friend has a Dad who I quite fancy. He was divorced years ago and as far as I and my son's friend knows, there's no one else around. Do I ask him out, or will it just be mortally embarrassing for ever after if he declined? If so, how do I do it? Strategies please?

So, said Dad has asked me and my son to go out for the day with them next week. I'm definitely invited! So pleased!

Any tips as to how to move it on to going out for a drink with him?

Find out what sort of interests he has while you are out and then say: "Oh, such and such [that he likes] is happening in [nearby town] next week. I'd quite like to go - would you like to come with me?"

Btw, it sounds as if you are pushing at an open door.

haha re your 'how to move', OP. just say after your day out, 'shall we go for a drink?', I'm sure it would be the most natural thing to say after a day together. Even if the drink is arranged fir next eve with no dc.

Find out when he is next DC-free.

Let him know when you are free also.

Then maybe casually mention meeting for a coffee/beer - as in 'Oh, I'll probably be in town that day, fancy meeting for a coffee/beer, could be fun to chat without the boys in tow?" Or something to that extent.

Be casual and lighthearted - imagine you are talking to a woman.