Should I DM first? If so, what should I say?

[Anonymous]

So backstory: I work in a shop and this woman has been trying to set me up with her nephew for years, I’ve always said no because I genuinely wasn’t looking but when she asked last week I was curious so I asked a bit about him and he seems like a great guy, I said no to her setting us up mostly because she wanted to bring him to the shop and 1 I’m literally working and 2 I think it’d be awkward for the both of us to talk in front of his aunt and my mom, but I did follow him on Instagram and he followed me back. Now I’m thinking about DMing first since I think he’s on the shy side but I’ve no idea on what to say since we’ve never spoken before and tbh I’m kinda shy too so I’m really nervous, also I have no clue if his aunt mentioned me and that’s why he followed back

Go for it

Wait and see if he texts first

[OlderAndWiser]

Ask him if he'd like to meet you for coffee when you get off work, but let him know that you will need to be somewhere else a bit later, so you'll only have like an hour to sit and talk. That means, no matter what happens, it won't last very long. And if it goes well, he can suggest a dinner date for later in the week.

[Danny_dan92]

Girls have been messaging first a lot lately. Maybe a society change

[Spencer10]

Life is short. Fortune favors the brave.