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I'm a project leader in a small (a few dozens employees) Spanish IT company. In one of my projects there is a 22yo female intern (I'm a 29yo male) who I'd like to flirt with.

I noticed my attraction to her recently and I realised yesterday that since then I unconsciously started provoking a lot more interactions with her (teasing, useful work discussions, etc). I have a playful nature with everybody so I honestly think nobody noticed. Also it looks like she enjoys this extra time I created so I guess she doesn't feel uncomfortable.

Now I'll try to spend time with her outside of work and see how she responds to that. Also our company organized a week-end with all the employees in 2 weeks and none of the bosses will be there so it should be kinda fun, although I'd then be one of the employees with the highest position.

I'm posting here because I don't know how to address this situation. I absolutely don't want to scare her off, to make her feel uncomfortable, trapped, threatened, or to make her think I'm trying to use my position to make her do something. And I don't want to see her uncomfortable if she turns me down nor do I want her not to turn me down just because of the remaining months until the end of her internship. Each time I think about an approach, the whole high position/intern, male/female, 29yo/22yo situation comes back at me and I feel like I'm facing a time bomb.

Any advice would be greatly appreciated.

PS: Not doing anything in the upcoming days/weeks is not an option.

PPS: My only concern is this situation taking place in work, where harassment, reputations and rumors do happen. I don't really care about this job, I know I would find another one if something bad happens there, my concern is focused on her.

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    This question seems to be attracting downvotes, but it appears to be a totally valid question. Just because you think the answer is "don't" doesn't mean the question should be downvoted. – Erik Aug 19 '18 at 10:15
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    "Not doing anything in the upcoming days/weeks is not an option.". Yes it is. Unless someone has your family hostage and will kill them unless you flirt, exercising self control is always an option. – DJClayworth Aug 19 '18 at 19:53
  • @DJClayworth She is leaving the country for 3 years after this internship. I think that if she's interested this could be a serious thing, thus possibly leading to following her there in the future. I can't do that if I don't even know what she's feeling or worse, if she doesn't feel anything. Thus I need to know, so I have to do something. I think I'll step back from the common projects so if she turns me down, her potential uncomfort would be limited as we won't have any reason to see each other during the day, and if she doesn't then I'll talk to HR. – CruzM0 Aug 19 '18 at 20:28
  • This does look like chasing after a woman, with the job being the complication. Your goal seems to be to have a relationship with the intern, and you mention many issues with the job. You don't seem to grasp that there is likely no way to keep this comfortable for her as long as you're at the company, and exploring the possibility will very likely make her uncomfortable. – David Thornley Aug 20 '18 at 18:24
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I think this is a very dangerous situation, and you are gravely underestimating it (google #metoo...).

Many large companies would give you a formal warning just for what you are doing already, and might terminate you with a very black mark if you continue. Abusing your position with an employee (or intern) is considered inacceptable, and as you are her manager, flirting is very near to abusing; you are putting her under a lot of pressure.

Maybe she likes you too, and everything could be fine between you. Then you are still in potential difficulties, as colleagues could complain about you prefering her over better qualified people, and giving her the most interesting work, etc. Most manager level trainings instill that you must avoid even the impression this could be happening at all cost - it does not matter that you maybe never 'preferred' her, just allowing people to think so is damaging the team, and your image and career.

Or, much worse, she is not interested. What should she do? Play along, and maybe even date with you, or have sex with you, in the hope to keep the job, or get a permanent position? Or tell you no, and lose her job and all chances? You cannot know that she really likes you as long as you are in a position of power in her life.

Seriously, the only clean way out is to either forget it completely, or - if you think you can't - talk tou your manager or HR, tell them that you have a romantic interest, and ask for her or you to be reassigned (if you are not willing to do that, you are not serious about her anyway, so forget her). Once you are not her manager, you can see if she is still interested (happy couples sometimes come from that).

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    Thank you for your thoughtful answer Maybe I wasn't clear, each of us have several projects and we have one project in common. Also I'm not her manager in any way so I can't give her a job (she's going to study in a distant country after the internship anyway so she doesn't want to stay here & she actually often repeats it to our bosses who already offered her a permanent position) and I can't give her interesting work. I'm leaning toward leaving the common project for now. And knowing happy couples come from that is actually why I want to try, as close friends of mine met as intern/manager – CruzM0 Aug 18 '18 at 22:38
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    @CruzM0 , sorry I might have gone a bit overboard, because of recent bad experiences. Rereading your question, I see that it doesn't fully apply to your situation. Consider it a related information. – Aganju Aug 18 '18 at 23:42
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    If this intern is under your project it would be inappropriate to flirt with this intern. It would also is inappropriate to transfer the intern to another project. Feel free to move off any project she is involved with though. – Donald Aug 19 '18 at 17:14
  • @Aganju don't be sorry, I get your points and see how they can apply to my particular situation – CruzM0 Aug 19 '18 at 18:13
  • She may not be below you, you might have no direct control over her, but what happens if you get together and it all turns sour? Who is the company going to get rid off? Men stick together who is going to be affected if you get really angry at her rejecting you, and she has no way of knowing how you may react, especially if you live in a place with almost zero employment laws (like large amounts of the USA). – WendyG Aug 20 '18 at 10:32
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I don't really care about this job, I know I would find another one if something bad happens there, my concern is focused on her.

You don't really care about this job, but the target of your affections might. Consider the position you could be putting her in.

You should find another job now, hand in your notice and leave this one. Then you can flirt all you wish with the intern where you used to work.

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    Best solution, I know a guy did this and married the girl eventually – Kilisi Aug 18 '18 at 21:42
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    Keep biz and pleasure separate. Survival 101. – Neo Aug 20 '18 at 12:13
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I don't know how to address this situation. I absolutely don't want to scare her off, to make her feel uncomfortable, trapped, threatened, or to make her think I'm trying to use my position to make her do something.

As a project lead you do not flirt with an intern while he/she is an intern.

If you two get along well so much that it would be more than an affair, then you should be able to keep that off until the internship is finished and you exchange phone numbers in a "if you would like to stay in touch" way.

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Many years ago, a colleague found a tactful way to find out if I were open to office romance in general. I found a newspaper on my desk open to the personal ads, with one of them highlighted.

If I had been open to office romance, I could have responded to the ad, through the newspaper's system for forwarding responses, and found out who it was. I was not interested, so I just ignored it.

The 21st century version might be to create an account on a dating web site, and leave a note of the web site URL and your account name (not related to your real name), on her desk.

Also our company organized a week-end with all the employees in 2 weeks and none of the bosses will be there so it should be kinda fun, although I'd then be one of the employees with the highest position.

Please be very careful during that weekend to keep your interactions with the intern to a minimum, and strictly professional. It is going to be hard for her to avoid you or get help in dealing with you, especially if you are one of the most senior present. Who should she turn to during the weekend to say "CruzM0 is making me feel uncomfortable. Please get him to be more professional."?

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    This is okay between peers or with people in separate parts of the organization, however when one person has a position of authority or influence with respect to the other person it is not okay to express a romantic or sexual interest. – Ben Mz Aug 19 '18 at 1:40

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