What’s a girl to do?

6 01 2008

There is this really nice and very attractive woman who works at the courthouse that I go to about once a week. She is a probation officer for a couple of my clients, so I see her or talk to her on a fairly regular basis.  She is the kind of woman I am typically attracted to; she has long hair, she doesn’t wear a lot, if any, make-up and she wears casual clothes. You know, nice but not too fancy. Anyway, she seems down to earth and smart. What I really like about her is that she doesn’t pull a power trip with her probationers. She has a genuineness about her that is really cool.

 My problem is this; I’m not quiet sure she’s “family”. That’s the problem with the woman I am attracted to. Unless they’re in a gay bar or P-town or something, you never can really tell what team they play for.  Friday must have been dress down Friday. She had on jeans, an  LL Bean ski coat and hiking boots. There you have it! She must be a lesbian! Not so fast readers, she also has long nails.  I do  know plenty of lipstick lesbos with long nails but it’s really throwing me off. Also, I have straight girlfriends who wear jeans and hiking boots. Ugh. So, if I call her up and ask her to coffee or something and she is NOT on my team, I risk embarrassing her and then our working relationship could be uncomfortable.  And let’s say she is a lesbian. Is it crossing professional boundaries for me to ask her out anyway? I don’t really think so since she works for the state and I work for a private non-profit. And let’s assume that she is playing on my team and she does want to go out with me. We would never be able to talk about the clients we have in common. That would be difficult. Not impossible though.

 I’ll see her in court next Monday, perhaps I will try to get more information then. Any advice would be helpful.




6 responses

6 01 2008

The thing I’d be worried about is what if you ask her out and she says yes and the sex is super hot and you wind up living together and 2 years from now you break up and THEN you have to work with her. That part would be awkward. But I’ve been told that I have a problem projecting and it hinders me in life.

Is there anyway you can ask her to join you for something (coffee, sandwich, football) that’s clearly not a date but a casual setting where it’d be simpler to drop “I SLEEP WITH CHICKS, WHAT ABOUT YOU?” into the conversation?

6 01 2008

Kizz, honestly? That’s what I’d worry about, too. It’s not just you.

Auntie, I think that Kizz’s suggestion is probably the best one, short of finding someone in the environment who might know what team the chick plays for. Can you find out if she’s got a Facebook or Myspace page? There might be some info there…

6 01 2008
Laurie B

Been there, done that. Not going to do that again, that’s for sure.

Kizz is so very right. You haven’t even talked with this woman and we’re all worried about the moving truck!

I mean, after all, it’s just a bit of time and some coffee or ice cream. You could ask her to go with you to hear some live music.

Cheryl Wheeler is always a good ice breaker and I think she’s going to be in your part of the world soon. Whether this woman is gay or straight, Cheryl will help you find out and her music is worth sharing anyway.

Friends first, a lengthy time of courting and dating, slow is good, (as frustrating as that may be), is what worked for us!

Keep us posted!

Laurie B

6 01 2008

Kizz, there will be no moving truck. Mrs. Chili, if she is smart, she would not have a myspace or facebook page. In that line of work you really don’t want people finding you. Dude offered to run her. My reply was ” That would be useful if they listed your sexual orientation on your BOP.” Thanks but no. Laurie B, music is good but it feels to much like a date. Friends first for sure!! Great advice, thanks.
I think I might ask her about her weekend and what she did for fun too try and get a better idea. What do you all think? I have been trying to think of an excuse to call her tomorrow…

6 01 2008
Laurie B


You’re right, music is a date. Not there yet.

A call about “Hey, we work in the same field and ya’know, it might be good to know each other, how about a coffee some day?”

Good luck, but I don’t think you’ll need it. Take a breath and be brave.

Meanwhile, we’re watching football and the Titans are stinking up the joint. We don’t want to play Jacksonville. The sweetie is just full of “oh, hell”. The way she says it just make me laugh.

Hope all goes well.
Laurie B

6 01 2008

Does everyone at work know you are a lesbian? If they do, and it’ a safe environment, I would start asking around. Maybe someone else knows more intimate details of her private life. Like in 101 Dalmatians, start working the barking chain.

If you are not out at work, I would start having regular coffee breaks or drinks after work. The worst that could happen is you end up with another cool straight girlfriend. Good luck! This whole dating thing is tricky shit.

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