Guest Posted November 23, 2006 Posted November 23, 2006 Let me preface what I am about to say by apologizing for the length and thanks ahead of time for those who provide meaningful advice. Anyway, here I go: I am a mid 20s male who is intrigued by a current situation that may or may not develop into something. There was a girl that I work with I always knew of who I thought was pretty cute and from what i could see had a excellent personality, but at the time she was in a relationship with another guy, so I really didn't approach her at all. Lets call her "Mildred". Fast forward to a couple of months ago, she is now single and so i figure that i would at least approach her and at least get to know her a little better. One problem: She was a supervisor. Although we are the same age she was still a supervisor, not my immediate supervisor, but high enough where anything more than friends would be inappropriate. Yet, we continued to talk more, joke around with each other, and I guess flirt (According to coworkers we were anyway). One day I am outside on a break with a friend of mine and he mentions a play that he wants to go see with his girlfriend, I mention that I could probably tickets for him. At this time "Mildred" comes out and sits next to me, my friend then says "Hey why don't me, Rachel, you and Mildred all go?" Essentially, he saved me the trouble of asking her myself. She agrees to go. Here is one of many questions, is this considered a double date? "Mildred" and I go through the various dates of the play and she selects one, a Friday night at 8pm. Which happens to be the same night that a mutual friend of ours is turning 21 which lends itself into a nice date (Play then drinks with a few friends) A few weeks have passed since the arrangements have been made and the "date" is coming in a week. Since that moment in time, Mildred and I have been getting closer and closer. We continue to joke around, flirt, and people say that she lights up when I'm around and that we are perfect together. I am reluctant to believe that. Anyway, last week she told me that she is leaving the company to go back to school and her last day is 11/22 (today). Immediately, I am thinking that I can now go forward and see what happens between her and i relationship wise. We exchanged phone numbers the other day under the guise of confirming the arrangements for the play. I knew I wasn't going to see her on her last day, so last night, I gave her a small going away present consisting of a xmas cd that she hinted that she wanted me to buy her as a going away present, a singing cow, and a few other things that are reflective of how we joked around. I left a note basically wishing her luck in school and thanks for making me laugh all the time. I left these items in her office. She later thanked me in a txt saying it was really sweet me of to do that. Now here comes the hard and potentially insecure stuff. 1)How long should I wait before I call her and see if a date presents itself? 2)Should i treat the play as a date or do you think she just agreed to go because it is simply something to do? 3)If the play is to be considered a date, should i make that the first date and if things go well, call her then and see if a second date develops with just her and me? I again thank everyone for their insight and I wish everyone a Happy Thanksgiving.
moman Posted November 23, 2006 Posted November 23, 2006 The play is a date. Go out, have a good time with Mildred, and be yourself. Do not be nervous. You are already overthinking the scenarios which is a recipe for certain disaster. Just go out with her, have a good time, and see what happens. Do not call her between now and then. If anything, text her the day before to figure out the logisitics (we'll meet at 7 PM at Barnes and Noble, etc). Any by any means, do NOT start talking about the second date before the end of the first. If she brings it up, say "sounds good, I'll give you a call sometime" and be vauge. If it doens't work out it's not the end of the world. Good luck.
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