A Working Girl's Dilemma

Dilemma….guy asked me out….guy I work with….don’t know what to do….



I hate it when I have to take the time and look at everything from both sides. Or rather when I don’t “take the time” but just have all sides of a situation hit me all of a sudden. I’ll be brushing my teeth and all of a sudden I’ll see where I could be in 3 weeks.


So, back to the dilemma. Somehow I turned a simple shopping trip at our company store into a lunch invitation from a co-worker that I recently met. I’ve been down this road once before with a coworker. I went out with him, we kept it all hush hush at work, and then it ended, and then it was awkward, ok, it still is! Here’s what went down: I picked up some items for a charity event from him last week, our first meeting. He told me that I was not what he was expecting; he was expecting a “older” woman. We laughed and then I headed out. Friday I went to our company’s associate night at our store. I got there about 45 minutes before my friend showed up so I looked around, tried on LOTS of shoes, found a new pea coat that’s adorable and will make me get rid of the blue one that I’ve had since 8th grade that comes nowhere close to fitting and then just hung out by the door waiting for Rebecca to show up. He saw me waiting, came over and talked for a little while. He asked who I was waiting for; when I said a friend he immediately asked if it was a guy or girl. I didn’t really think about it, except for the fact that Friday night is supposed to be only for associates and family members, but I responded that it was a girl. I was relieved that he didn’t seem to see a problem with this. So Rebecca got there and she had her niece with her, we started looking around for some bedding and he saw me wandering with Rebecca’s niece and was very accommodating when I asked for a place to put our stuff so we didn’t have to haul it all over the store with us. We got done shopping and went to check out and who should check us out but this particular guy…go figure huh?! We chatted about the charity items and he made some remark about me not responding to my e-mails and I said that I do, I just sometimes take longer than other people. So in all my wisdom as I was pulling into the next stop for the evening I responded to his last e-mail that he had sent two days prior and just said thanks for helping with the charity items. About 2 hours later I got a response from him asking me to go to lunch with him this week. Uh…possibility?


So these are the scenarios that flash through my mind. #1. Our lunch goes really well, we laugh a lot, we have a good time together. We become friends. Not awkward, it’s actually ok. #2. Lunch is great, he asks me out again, we start seeing each other…and then it doesn’t work and it becomes awkward cause he’s my contact for Charity items. #3. Lunch is HORRIBLE, I feel weird, I don’t know what to talk about and then it’s just odd from there on out. #4. I decline his lunch invitation, hurt his feelings and he acts weird from there on out. #5. I decline his lunch invitation and miss out on any opportunities with him. The problem with seeing all of these possibilities is that it inhibits me from making a decision either way. I basically freeze. I just don’t know what to do. I hate making decisions like this. Do I go, do I not go? Other co-workers would say “Run the other way, don’t personalize work!” Some would say, “What could it hurt? One lunch doesn’t determine anything.” So I ask the universe the question…what should I do?