I am trying to send an email to my UK buddy. I have outlook, he has gmail. There is nothing showing in my sent box, I have received no reply. Has anyone else had similar issues?

Being Gmail maybe there's a current 'google issue' with it. Did you try sending it using a VPN?

Nope I don’t have one right now

Just remembered my old gmail account so I tried w/without VPN and it's definitely a firewall issue as it works with VPN but not without.

This page has a list of free VPN's you can use if you want to get that email sent : www.templatemonster.com/blog/free-online-vpn-services/

Rereading it I see it's your buddy in UK using gmail so actually not sure now, duh!
Maybe the firewall doesn't like the gmail address? Best guess and is a guess.

@tiger

I hope you're not trying to contact that weed seller who left his gmail address ;)

Weirdly any mail I sent to my gmail ends in spam folder so again, another option as to why.

It went through eventually, it took about an hour. So I guess a fur wall issue. Either a net neutrality (lack of) issue, or vetting, or buggerance factor.