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The Perfect In?

NeverTrump

NeverTrump

Exposing GOP since 2015
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Here's a situation I am having with a soon to be ex-co-worker over the past three years. We both started here at about the same time and quickly started a flirty thing (as far as I know). Nothing ever happened because she is older and has a kid and is a a director at my organization. I wanted no part in that when I was 25. But now that she is leaving, things have been... escalating. I think?

I worked with her on a project a few days ago and when I was finished we talked about her future plans where she was going etc... I told her I'll miss her and we hugged/held hands. It was very sweet. Today she came into my office (I share with co-workers) to say goodbye to them but she kept winking at me and explaining how single she was. How happy she will be to get some time to travel in between jobs and the great work she will be doing.

On top of being drop dead gorgeous, and totally out of this nerd's league, she's a high powered attorney working for the city. I really have no idea if she likes me in the way that I like her, or if she's just really super friendly, but all the signs seem to be there. I would love to get a chance to attempt to sweep her off her feet, but I think asking her to catch up once she gets settled at her new job is a bit too casual.
 
Casual is the best way to do it. As great as women are, they're not as complex as men are when it comes to having asking them out on a date. Make your intentions known, say something suave and that's your in right there.
 
CMPancake said:
Casual is the best way to do it. As great as women are, they're not as complex as men are when it comes to having asking them out on a date. Make your intentions known, say something suave and that's your in right there.
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Is there something more I can say than, "let's get coffee when you get settled in at your new company?" I mean I do want to hear all about it, but there has to be a way to let her know I have a romantic interest too. Everything I think of to add to that sounds creepy.
 
NeverTrumpGOP said:
Here's a situation I am having with a soon to be ex-co-worker over the past three years. We both started here at about the same time and quickly started a flirty thing (as far as I know). Nothing ever happened because she is older and has a kid and is a a director at my organization. I wanted no part in that when I was 25. But now that she is leaving, things have been... escalating. I think?

I worked with her on a project a few days ago and when I was finished we talked about her future plans where she was going etc... I told her I'll miss her and we hugged/held hands. It was very sweet. Today she came into my office (I share with co-workers) to say goodbye to them but she kept winking at me and explaining how single she was. How happy she will be to get some time to travel in between jobs and the great work she will be doing.

On top of being drop dead gorgeous, and totally out of this nerd's league, she's a high powered attorney working for the city. I really have no idea if she likes me in the way that I like her, or if she's just really super friendly, but all the signs seem to be there. I would love to get a chance to attempt to sweep her off her feet, but I think asking her to catch up once she gets settled at her new job is a bit too casual.
Click to expand...

Shoot her a text or facebook message asking if she wants to get a drink sometime. Nothing more than that. If she says yes, cool! Go have a CASUAL drink or two. Don't get messed up.* Let things go where they go.

If she says she's too busy, forget it, unless she gets back to you when she's not.

* -- unless she starts ripping shots like she's Marion Crane in Raiders of the Lost Ark, in which case, go to town son
 
NeverTrumpGOP said:
Is there something more I can say than, "let's get coffee when you get settled in at your new company?" I mean I do want to hear all about it, but there has to be a way to let her know I have a romantic interest too. Everything I think of to add to that sounds creepy.
Click to expand...

Let the romantic interest come naturally. Don't force it. If she's into you, you'll know.
 
CMPancake said:
Casual is the best way to do it. As great as women are, they're not as complex as men are when it comes to having asking them out on a date. Make your intentions known, say something suave and that's your in right there.
Click to expand...

Nooooo. No no no no no.

Far too often, "sauve" comes off as "super desperate with an extra side of creepy." Just be yourself. Keep it casual. No cheesy lines, nothing like that.

Wait a week or two and then text: "Hey, <insert name here>, hope the new job's going well! Office isn't the same without you! You want to meet up for a drink later and tell me about the new gig?"

^ that.
 
NeverTrumpGOP said:
Here's a situation I am having with a soon to be ex-co-worker over the past three years. We both started here at about the same time and quickly started a flirty thing (as far as I know). Nothing ever happened because she is older and has a kid and is a a director at my organization. I wanted no part in that when I was 25. But now that she is leaving, things have been... escalating. I think?

I worked with her on a project a few days ago and when I was finished we talked about her future plans where she was going etc... I told her I'll miss her and we hugged/held hands. It was very sweet. Today she came into my office (I share with co-workers) to say goodbye to them but she kept winking at me and explaining how single she was. How happy she will be to get some time to travel in between jobs and the great work she will be doing.

On top of being drop dead gorgeous, and totally out of this nerd's league, she's a high powered attorney working for the city. I really have no idea if she likes me in the way that I like her, or if she's just really super friendly, but all the signs seem to be there. I would love to get a chance to attempt to sweep her off her feet, but I think asking her to catch up once she gets settled at her new job is a bit too casual.
Click to expand...




the first thing that came to mind...:lol:


Ask, the worst she can say is no.

When it comes to most things in life, especially with the ladies, I find that I do not regret the things I've done, but those I did not do...
 
Kobie said:
Wait a week or two and then text: "Hey, <insert name here>, hope the new job's going well! Office isn't the same without you! You want to meet up for a drink later and tell me about the new gig?"

^ that.
Click to expand...

I think the office isn't the same without you line is perfect. We are friends on Facebook and she was bragging about that too :) so I think a yes is almost certain. Even if she doesn't want anything too serious. She's still good friends with the ex and all that. Though she is always busy. She's going on her trip for new years so i might wait until after that to officially ask. I'll start with the emails before that tho. The have fun on your trip type stuff. Just to pick up where we left in the office.


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Just ask her out man. If you guys held hands, she winks at you, and talks about being single it's about as clear a message as you are ever going to get. Go out to dinner, don't drink too much, and don't be afraid to open up a little. Try not to put too much pressure on yourself.
 
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