How can I flirt with an older guy at work?

[Anonymous]

We do flirt sometimes but what can I do to show him that I really like him more than a fiend. I’ve had feelings for him for a year now and we have always been close.
I’ve never had feelings for someone I work with before so am unsure on how to handle it.
My workplace is fine with people dating. And I know he’s single I just don’t know how to act around him at work because I don’t want to scare him away..
He’s 48 and I’m 30 so I don’t even know if he’s interested in me that way anyway…

[Lockey_]

Starting relationships at work is always problematic because often the work stays longer in life than the relationship. So in case the relationship ends before the work ends, both of you got to deal with the reactions of co-workers and even worse, your new parterns know about that you see and interact with your ex-partner every day.

If the guy is 50, he might most likely think about that the current job is the last job he ever will have in his life. So my recommendation is that you take it easy and out from work into private. For example it might be neccessary to keep your private relationship secret at work for about 1-2 years or such...

[CasuallySamsonite]

Is he your boss?
Do you guys hang out / interact off the clock or outside work?
as long as he's not in your direct chain of superiors, my advice would be to find a moment alone with him an casually brooch the subject outside of the workplace, Ideally, over drinks... like, after the second round before the third. Just see what he says... if it's a hard no from him, then you gotta commit to never, ever bringing it up again (unless he does) otherwise, it's still good idea to keep it on the down low unless HR has specific regs for declaring relationships within the office... but even there, I'd not rush that. Good luck. Whatever his answer, he's a lucky bastard XD

[Asker]

Thanks for your advice!!

No he’s not my boss. We do text each other sometimes and he messages me sometimes on Instagram etc asking me what I’m upto, or likes my photos. But apart from that nothing.

We have went out for drinks with our whole office once and he was drunk and told me he liked me but I think he just meant as a friend. It’s really hard to tell and why it’s messing with my head so much. 😞

[honeynut-scenarios]

Turn casual conversation into more personal questions. Smile often, and tease a little. You can turn his name into a Nick name, for example, If his name is Tim, address him as Timmy or Timberly. Do small favors. Buy him breakfast one morning. If any of this is reciprocated, he’s interested. Don’t do too much tho. Pay attention to how he responds.

[chefsam]

He probably knows you like him. But if you really like him, make the first move & ask him out. The worst that’s gonna happen is he says no. You don’t wanna overthink things and drive yourself crazy thinking about if you should or shouldn’t. The longer you wait, the higher chance he meets someone new & you missed your chance

[MTC29]

Invite him to lunch. Lunch is "safe", as opposed to dinner, which has implications of things which might follow. If he says yes to lunch, then you are on the right track. If he declines your invitation, move on because he's not interested.

[Anonymous]

Don't bother. He knows you're interested. If he wanted something more he would have made a move by now. If he's single at that age, it's more likely because he wants to be.

[Asker]

How would he know I’m interested?

[Opinion Owner]

It shows through body language, tone of voice, eyes, proximity and action. A man his age is likely to have picked up on it.

[Anonymous]

As a female, you literally have all the power.
If he is paying attention to you at all... he likes you.
Make a move.

[Asker]

How do I have all the power? I feel hopeless here haha!

[Opinion Owner]

You are the sex that gets to pick and choose when and with whom you have sex.

you literally are the ones who have all the power.
You just don’t make the move because you expect men to make it.

[Aakash_Hangargi]

Do you think it will turn into relationship?

[Asker]

I don’t know if he would ever think of me in that sense unfortunately…he’s just such a great guy.

[Aakash_Hangargi]

Is he married?

[Asker]

No he’s single

[Aakash_Hangargi]

Take the leap and know for yourself

[Anonymous]

You give me hope. I’d love to have a woman years younger than me be interested in me.

[Asker]

Haha! I didn’t expect to ever feel this way about someone older but he’s great…that’s why I’m so terrified incase I’ve got it completely wrong and he’s just being nice to me haha!

[Danny_dan92]

By quitting your job first

[Subarugirl]

Don’t date coworkers… just don’t