Broke up with fiancee, now back to dating - work relationship (is it a date?)

[kenzo1920]

Hello internet!

 

Background: 26, male, 5 months ago I broke up with my fiancee after 4 years of being together - we had it coming for a couple of months, in the last stages she was emotionally and verbally abusive so thankfully I was able to get back to my normal self rather quickly... and started now dating again. Or did I?

 

I'm a co-founder in a quickly going startup (1xx employees) and a girl whom I knew from school joined us a few months back as one of the managers (I recruited her). We have a rather open culture so we ended up in a number of social situations where we talked quite a lot. I was rather cautious about the whole thing as I would never date a co-worker/employee, but to keep it all very hygienic I made sure that there is no direct reporting line or conflict of interest when I figured there might be something to it.

 

One thing led to another, we started ending in more and more one-on-one situations where we're both clearly comfortable and spend a lot of time together, but at the same time it's rarely a flirty situation - we have a lot of topics in common (friends, cultural stuff... so conversations can go on for hours).

 

I would never want to make her feel uncomfortable and am very cautious about the work side of things and started dropping some very subtle hints, flirty words etc, and since that landed rather well (even though the initiative was mostly on my side), I invited her for a dinner - we had a great time (a lot of talking again!), went for a walk, spent some time in my apartment over wine but I guess we both didn't know what to expect so it ended up being just that -a long "conversation date".

 

Fast forward a couple weeks, we're still very friendly, there is a great communication both in and out of work - in the meantime we sent each other photos and stories from vacations and had some work lunches together a number of times.

 

This week I invited her for dinner to my place, where we ended up chatting for a long time again, then I walked her home and we stopped at a bar on the way to chat a bit more. We were both definitely very comfortable and again, the whole thing lasted maybe 6 hours.

 

Now here's the issue: on one hand there's a great connection and we're definitely enjoying each other's company. On the other hand, given the amount of time the thing has been going on (2-3 months, 2 "dates" - in my book if you invite somebody for dinner it's definitely a date, no?) - I feel uncomfortable with the fact that it still only feels half-romantic - should I be making my intentions more prominent and stop being a pussy or maybe is it better to give it some breathing space? Usually when things are getting flirty I can easily bring things home, but I've never been very good in situations where I need to take initiative and be the flirty, touchy and "pushier" person.

 

We went on two dates, talk a lot, have a connection - on the other hand, I have a feeling that even though she has a very open personality and is generally a very social person (very friendly towards people, a little bit touchy), she has a slightly different attitude towards me - that's the part which I don't feel comfortable with - we talk a lot, there is a lot of eye contact, but very little of those typical flirty things, touching etc. What would you advise, should I push it a bit more and try creating some romantic environment? We keep ending up in situations that make me uncomfortable because there's no way to make a move - e.g. when I walk her home to her door, we walk next to each other and she kissed me goodbye on the cheek, but if I wanted to kiss her it could be a bit awkward - there is half a step too much between us to make it smooth. Maybe I'm just hopelessly bad at closing those kinds of situations? Or is it possible she's still trying to keep me at distance? But then why would we be going out on dates? Or maybe, since she knows about my recent relationship even though we didn't talk about it directly, she doesn't want to push too much?

[GemmaUK]

Sounds like she wasn't aware that these were 'dates'.

You're not giving her the opportunity to make her own choice as to whether she wants to go on a date with you simply by not specifying it's a date.

Dinner at someone's home who I used to go to school with - I wouldn't consider to be a date.

[LifeBeginsAt40]

My new girlfriend is a work colleague. Similar situation to yourself - was with my ex for nearly 5 years, and knew my new GF for about 3 of those. Lots of flirting at work, lots of jokes and laughter. She asked me out for a drink about 2 years ago, but I had to decline. Split up with the ex just after xmas and thought hey, I'm gonna go into work and straight up ask her out.

 

So that is what I did. Took a few weeks to organise a time to meet, and then it was just fireworks, magic etc etc. Here we are now as a couple. We have talked about the past few years, and she said that when I asked her out she wasn't sure if it was a date or just as friends. She said that of course she felt a spark between us too, but didn't want to assume that there was anything on my part.

 

My learning point from all of this was that where as I saw it 100% as a date, she didn't. I don't think it matters though. If it is just the two of you out having fun, then see what happens. If she is giving you loads of green lights I would say she is definitely open to the prospect of more. When I went out with my GF on our first (?) date, she was really open to me putting my arms round her, leaning in, flirting with her etc etc. I got the right signals, leant in and went for the kiss. The rest is history.

 

I would say on your next night together, why not just give it a go and see what happens? Might be awkward with work if she backs away, so you have to be reasonably certain she is digging you, but wouldn't you rather know than wonder for the rest of your life?

[introverted1]

I think you need to stop and think about her for a moment.

 

She works at the company you founded. If things were to go south, it's pretty clear who'd be on the outs. If you care about her at all, why would you put her in that position?

 

Find someone to date who doesn't work for you.

[kenzo1920]

@introverted1 - fully get your point and I wouldn't even think about it if I didn't take it seriously.

 

On the other hand, it's a bit more complex than that - she doesn't work "for" me directly and if things got really serious I would be ready to leave the company to attend my other businesses. If things do not work out for whatever reason I'm sure that we will both be able to continue working in the same company without much issues as we do not have many direct touchpoints.

[d0nnivain]

Stop!

 

If you own this company you cannot date a woman you recruited to work there, unless at the end of the relationship you want her to own the company. What you are doing is sexual harassment of an employee. Cut it out now. It doesn't matter if you don't have many touch points. If she draws a pay check from a company where you have an ownership interest this is a lawsuit waiting to happen.

 

If you "leave the company" unless that means you get bought out of your shares, you will always be her boss & that is a huge no go.

 

Do your co-owners know you are doing this? You are putting their economic well being in issue too.

 

Your better option would be to cool things down & find her a new job at a company you have no interest in.

[introverted1]

@introverted1 - fully get your point and I wouldn't even think about it if I didn't take it seriously.

 

On the other hand, it's a bit more complex than that - she doesn't work "for" me directly and if things got really serious I would be ready to leave the company to attend my other businesses. If things do not work out for whatever reason I'm sure that we will both be able to continue working in the same company without much issues as we do not have many direct touchpoints.

 

You're the founder so, yes, she works FOR YOU, even if you have placed someone else as her direct manager.

 

I work at a smaller company (~100) employees and I was recruited by the owner. If he ever tried to date me, it would make my position untenable. Not only would other employees resent the relationship (and trust me, no matter how much you think others aren't aware, I can guarantee they are), but I would, too!

 

It is completely inappropriate.

[kenzo1920]

Understood. I'm pretty sure it doesn't change much, but in terms of my position, think first employee/C-level/x% share rather than CEO/founder (that also means she's not only not reporting to me but she's directly under the CEO). For other reasons I also know that we will sell the company in the next 1-2 years and I know the whole setup won't be permanent... that's why I tend to put a bit less weight on the circumstances...

[act00]

Dating a coworker is always a slippery slope, but you as the business owner or "top dog," it makes things a little more precarious. She may be attracted to you, but doesn't want to "go there." This could damage her professionally. Women are more likely to be accused of "banging the boss" and "sleeping her way to the top," and no one needs that reputation. I wouldn't go so far as to call this harassment, but you don't know what other people's perceptions are or if she may feel she's being placed in a position that her job is in jeopardy if she refuses your advances. The aftermath of having to work with someone when a relationship goes bad isn't that appealing either...and you're the boss.

 

Removing the job and work situation from the equation, I don't understand why you haven't taken some initiative and touched her. Walking her home, you could have held her hand. Watching a movie, sit next to her on the couch and put your arm around her. If she's not interested in you romantically, she'll let you know. I mean, unless she is purposefully and deliberately putting a large amount of space between you, she's probably making herself available to close the gap. Given that you're the owner of the company, and she doesn't want to make any assumptions on your interest level, it's probably stonewalling her making any advances. You walking me home, I probably would have taken your arm...if you weren't my boss.

 

A couple years ago, a coworker, someone who would be considered a superior, asked me out, and there was a lot of question on my part if this was a date or not. I was interested, yes, and thought it was mutual and this was a date, but I wasn't going to take that leap on his intentions...I just couldn't go there.

 

I'm thinking a talk needs to be had, which isn't necessarily romantic, but I think given your position in the company, it's a good idea to let her know you'd like to step things up, and to ask and see if she wants to give this a try and how you're going to manage in the work place, etc. Me and this guy, we agreed to keep it private...a lot having to do with that reputation...office gossip, etc. Things were off and on with us, and it was hard for me having to have contact with him when we were on the off, but neither of us, and me the wounded party, didn't let that affect the professional relationship. We also didn't reach any level of long-term togetherness. He wasn't really in a direct line of supervisor or manager, but it would have been that much harder if he was or if I was. Thankfully, he also wasn't an a**. Someone who's bitter and out for blood could make things really, really difficult.

 

I'm leaning in the direction of not getting involved with your subordinate especially given your position.

[d0nnivain]

Then date her after you sell the company.

 

You think you know her. You think you will be OK if you break up. Famous last words.

 

Instead when you break up & she's hurt & upset, when she runs to a lawyer what she's going to say will sound more like this:

 

He recruited me. As soon as I got there, he started coming on to me. Dinner at his house etc. It felt like I couldn't say no

so

eventually to keep my job I slept with him. Now I can't eat or sleep. My self esteem is in the toilet. I can't work. I can't even interview for a new job because I'

m

such a mess over this.

 

In this age of #MeToo do names like Harvey Weinstein, Bill Cosby, Rodger Ailes & Matt Lauer mean nothing to you?