Help with a coworker

[Thomasalexander]

So I want to have sex or at least fool around with one of my coworkers and I need advice on how to ask her. It’s a long a complicated story so hear me out. I’ve know her for almost 3 years now. I know she likes me and wants to be something like a couple but I’m not looking for anything like that. About two years ago now we talked about having sex and sexual things almost on a nightly basis. I think it was me who enjoyed the talking more then she did. I asked her if we could do something and her response was always I’ll think about it. We’d talk dirty, and one night we had a plan to do something but that didn’t work out. We kinda drifted apart and didn’t talk as much as the we did a few years ago. I know she’s concerned about how she looks as she’s a little overweight and she is also a virgin. I grab her tits and ass frequent and I’ve went as far as to reach in her shirt. So it’s been two years since we first talked about it and we have got to know each other a lot more since. That’s why I’m thinking maybe it would work this time. Any advice on how to ask her without offending her, and obviously I’m not going to force her into anything. I would like to find a way to make it fun and comfortable for the both of us and not just me. Like I said I just want to have sex with her. She’s a nice girl but we have many differences on major things for a relationship.

[Runesmith]

Let's take a look at what you wrote:

• I know she likes me and wants to be something like a couple
• I think it was me who enjoyed the talking more then she did.
• her response was always I’ll think about it

What does this tell you? She is (or was) not considering casual sex. And you know why - "and she is also a virgin."

Even in a progressive liberal country like Germany, the first time a girl has sex is a big deal to her (especially when she is out of her teens). She would want it to be with someone special. She considers you a friend (and maybe a friend with benefits in the future), but not that "someone special."

So you have two alternatives. Either you wait for her to lose her virginity with someone special, and wait for that to fall apart so that she will come back to you for break-up sex, or you need to be that someone special.

And if you want to be that someone special, you will have to try harder. In your entire post, I fail to see you trying to understand her or empathize with her - you are simply trying to get her in bed. And in your post, you explicitly rule out being that special someone - you don't want a relationship. If you want to pretend to be that special someone and yet be emotionally detached enough to dump her as soon as you deflower her - you would have to be a high-functioning sociopath, and unfortunately for you, you aren't a high-functioning one. If you were, you wouldn't be asking for advice.

There is a silver lining in this cloud. Intimate relationships with co-workers is best avoided, especially if you are a man. With your level of sociopathy you are on track to reach middle management (or in a small company, even senior management) - and if she gets pissed at you, all she needs to do is complain of sexual harassment... and all those explicit text messages you sent her would work against you.

Executive summary: you don't have a chance with her. Focus your energy somewhere else.