What happens when the guy is shy and he is interested?

[Sailormoon95]

I’m trying to give and send signals that I’m interested, but he is the shy type of guy too. Keep in mind that this was a huuuge set up with my upper bosses for THE longest time ever. Also, was not aware that he was interested in me. Do I just outright tell him that I’m interested? Or wait till he gives and send the next signal? Cus I have a feeling that we’re taking this sloooow.

[Guy13]

Workplace interests are usually shy for protection reasons. Favoritism of upper management is assumed. I would run the other way if your were suggestive or flirting with me at work. I own one outright and partnered in two companies and would consider your judgment poor. NO OFFENSE intended.

[Sailormoon95]

The thing is I know him outside of work too. He’s one of my good friends. Also, one of my policies at work is no dating or hooking up.

[Guy13]

No one is going to risk their job for you. Most will resent you if the idea is pushed. Dating is never easy... In so many, ways getting off the ground is impossible.

[Sailormoon95]

But this so called guy is apparently a good friend of one of my upper bossses and apparently has been interested in me. I’m one of the upper bosses and I NEVER date anyone at work. So technically, it’s like an outside conversation thing because I have a huge opportunity with my newer upper bosses after graduating.

[Guy13]

Damn…you got it going on everywhere, don’t you. Enterprising and multiple ball tosser.

[Sailormoon95]

Just wondering 'Guy13', may I ask who you are?

[Guy13]

I’m a “normal guy”. What ya mean?

[spartan55]

What do you mean, a 'setup with your upper bosses' ?

[Sailormoon95]

My new higher up boss after graduation said that he knows someone that might be interested in me told me that one of his friends and his family approve of this marriage if we were to date. But I’m hesitant because I have a strict policy for everyone to not date or hook up in business.

[Daurban6999]

I'm a shy guy. Take it from me just ask him out on a date.

[Sailormoon95]

Yeeeah but I always take the risk and get rejected. And I ALWAYS end up with. These shy guys. Plus I’m an upper boss so I like to be submissive and want the man to be in control because my dad is in control of his household just like any man should be.

[In_Trance]

nothing happens aside from you posting on the internet about it

[Sailormoon95]

Because I’m afraid of getting hurt and I’m shy. It’s not like they’ll ever no this is going to happen.

[boggboss]

If he is shy u will need to make a actual move lol

[Sailormoon95]

But how? I actually found him here on gag. You think this his way of making a move on me because he’s reading my questions and opinions?

[boggboss]

No I don't think that's him making a move if he hasn't actually done so