How do I ask him out???

iVillage Member
Registered: 05-30-2006
How do I ask him out???
2
Mon, 10-30-2006 - 4:11pm

Hi all,

I'm in dire need of anonymous, whole-hearted advice. I feel like I need a little more confidence before I pull this off, even though I already have my girlfriends behind me.

Here's the deal...

I recently decided to get a part-time "fun" job to help pay off some debt and fund a vacation I'm going on. It's a banquet serving job at a hotel, and I actually love it. I've worked there for 3 months. About a month into the job, I started having dreams about my boss's boss, we'll call him Kyle. Nothing sexual at all, just dreams that we were together/dating/whatever. I have about one dream each week, and over time, I've become more and more attracted to him. And the more I've talked to him, the more I'm liking him.

In a non-agressive way, I found out Kyle is single. He flirts a little, ate lunch with me last week (on a work break in the cafeteria), and jokes around. I told him last Saturday over our lunch break that it would be nice to know him in regular clothes. We flirt at work, but neither of us have made a move.

I feel that due to Kyle's position (being my boss's boss), he is a little restricted. I've never asked a guy out before, so I'm a little hesitant (not for any other reason that fear of rejection). Today, I won tickets to a hockey game next week....perfect opportunity. I'm working with him tonight.....help me!! What do I say? How can I bring it up? How can I do it casually so we're both comfortable, no matter what the outcome??

Help girls, I need a boost of guts!!!!

iVillage Member
Registered: 10-17-2002
Mon, 10-30-2006 - 4:28pm

Umm, sorry to burst your bubble, but personally, I wouldn't.

131.gif image by y_baros th5K.gif image by jade_simo

iVillage Member
Registered: 04-14-2003
Mon, 10-30-2006 - 7:07pm
How long to you plan to be at this place of employment? If your tenure at this position is limited, you can ask whether he enjoys hockey and explain the circumstances of the free tickets. He might go or not, but if you plan to be an employee for an extended period of time you might search for love elsewhere.