To not know when it's ok to ask someone for a character reference?

[MrsNextDoor]

I need a character reference...two really...and I have a selection of people to ask but don't know when it's ok to ask and when it's pushy.

One candidate is a lawyer...he's the Father of one of my DC's friends. They've been friends for 6 years since reception and though they go to different schools now, have stayed in touch via us parents...playdates and party invitations and trips to the park etc.

Could I ask him? He's the one who accompanies his DC to the playdates with mine so we're on good chatty terms but not exactly friends.

Do I ask in person or via text....I thought text so that I wouldn't put him on the spot but DH says in person.

Ask him text him saying the next time you see him you want to speak about a character reference then you dont feel on the spot

You would like not want want sounds demanding

Oh I feel shy! How silly is that!? It's so...un-me to ask for such a thing!

It is a bit of an awkward ask i had to get 1 years ago i asked ateacher at dds school

I agree with DH. You should ask in person.

"John, I am applying for XXX and need two character witnesses. I was wondering if you would consider providing me with one. I would truly appreciate it, but if you would prefer not, it's not a problem, I can ask someone else."

Simple, not pushy, and gives him an 'out' without feeling he's letting you down.