A
male
age
36-40,
anonymous
writes:Back in December I attended a Christmas work party. They had hired some hostesses to go around the party and offer different food and drinks. I spoke to one of them and she seemed more receptive to conversation than the others. I spoke to her a few more times when we would run into each other and finally got the courage to ask her out. She smiled and said "Maybe" then I said, cool, do you want to give me your Instagram or number? And then she smiled again and in a playful tone said "I'm not that easy" and walked away. I unfortunately did not run into her again and left the party. I'm 36 and she looked like she was in her late twenties, early thirties. Fast forward to last night and I was working another event for the same company and she happened to be there prepping to serve food again with her coworkers. I remembered her name, we'll call her Allison, and she remembered mine too. We talked a bit and she was open and flirty. But I had to get back to work (I was filming for the event). Later on since I had to film the guests eating, I walked on by and when her eyes met mine she smiled as I passed by. So lunch was over and they were packing up and I came by to ask her for her number, Instagram, anything, but she was still talking to her other coworkers and putting stuff away. So then I saw her take a large tray and head to the back. I thought to myself, well I'll just ask her when she comes back and busied myself. But she never did. I headed towards where she went about 3 minutes later and found out the exit door was right next to the large indoor trash can where she had thrown the plastic tray. So now I feel really dumb. Should I have just asked her in the vicinity of her coworkers? Should I have followed her? She really seemed like she might've even agreed to go out. I know I shouldn't have assumed that she would come back. That informed my decision to not be more determined in asking her out when she was just a few feet from me. Even if she wouldn't have agreed, I would've 100% preferred a no rather than this "what could have been" regret that's floating around in my head now. So anyway, I'm looking for any motivational words or advice to not let this happen again, to not be afraid of what others might think. Or did I do right in not trying again considering her last response was a maybe? Was she just toying and doing her job as a friendly hostess/server? I don't know. Thank you for any help!
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female
reader, anonymous, writes (28 March 2024): life is too short to miss opportunity but also to waste time lingering for somebody. I have been a huge believer in, one time a hesitation on either side but then either ask or say yes, which ever way round it happened to be.
Worst case scenario, they say no thankyou! but you get to move forward and don't play to peoples silly games.
Or they say yes and you move forward together.
I do not believe in games and playing hard to get, either somebody wants to be with you or they don't. Really life is way too short for messing about wondering. lovely opportunities can lay ahead in life and should'nt be wasted all because some body wants to keep a person in one spot of not knowing.
Make it nice, romantic even, quite, at the right time,clear and direct and wait for your answer but no games and waiting until that person pulls the strings, it's not good for the soul or mind. Adenturous spirits take opportunities and run with it. Good Luck.
I have no regrets in my life because i took every opportunity that I wanted, some worked some did'nt.
Go for it but 3 strikes and well out for me.
A
female
reader, Honeypie + ♥, writes (27 March 2024):
 I know that you meant well, it's kind of clear to see. However, you seem a bit oblivious that the woman was WORKING an event, SHE wasn't there for men to hit on her.
At the first even, she turned you down in the NICEST way she could think of, and you ignored that when you saw her a second time.
OP, DO NOT hit on people who are working an event. That goes for a cashier or server at a restaurant. THEY ARE WORKING! They cannot just "walk away" and avoid guys hitting on them. It's AWKWARD! HER "flirting" is her trying to be "charming" while working, it's kind of expected that servers either say very little or that they put on the charm.
I know these days it's extra hard for men to meet and ask out women (unless they use some swipe app) because it's quite often seen as "pestering" rather than a compliment/asking out.
BUT you got to have some situational awareness, OP
Perhaps in the future if you met a cute woman you want to ask out, ASK her if you can give her YOUR card, and if she wants, she can text/call you. That way she doesn't HAVE to reject you right then and there. And she doesn't have to give out her info if she doesn't want to.
As someone who worked as a bartender in my 20's - I was working not trying to have men pick me up or hit on me. Sure, I could be flirty and having banter - if I had time, but I NEVER gave out my number. And I never called ANY of them guy who gave me theirs.
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A
female
reader, mystiquek + ♥, writes (27 March 2024):
 It isnt that you handled anything wrong, its just that the girl wasn't interested and didn't want to cause a big scene or feel uncomfortable so she basically slipped out the back door. She didn't want to come right out and say no so she snuck out. Don't feel bad as it is said "nothing ventured, nothing gained". Trust me if a girl is interested...they will let you know. Most women wont make you chase them they will show interest and you will know it. You did nothing wrong so don't be hard on yourself.
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A
female
reader, anonymous, writes (26 March 2024): Here’s one encouraging thing: you are not afraid to hear the dreaded “no” and that’s a good thing ! Next time just use it with someone who’s actually interested.
She wasn’t playing hard to get. If anything, she was being polite when she said “maybe”. Had she been really interested she would not have let you slip away.
Women, even the younger women, are still thinking about men’s fragile egos. Turning men’s advances is a tricky thing. You don’t want to be rude and hurt their feelings AND you don’t want to provoke their anger, that’s for sure.
She didn’t know you. You were just a guy who asked for her number and she didn’t want to give it to you. She found a nice solution and hoped for the best.
The second time around, she was also just being nice. Had she wanted anything more she would have made a move. At least she would have given you an opportunity to be alone with her. She made her wishes clear and you did a good thing that you didn’t follow her. That would have been predatory! No woman likes to be followed period.
Also, no woman likes to be put on the spot and asked out in front of her colleagues, friends, strangers, anybody for that matter. It makes it harder for her to tell you that she doesn’t want to go out with you when there’s everybody watching. Some men use this to put pressure, they’re being so nice and if she says no that she’s the bad guy. So, you also did a good thing by not asking her out in front of people.
So, next time when you decide to give it another shot, be nice and direct. Tell her that you have no wish to be a nuisance and give her your contacts. She will feel much safer, in control and respected. Why should she be the one who gives her contacts?! This way if she’s interested, she’ll contact you, if not, well you have nothing to lose.
Let me put your mind at ease. I hope that other people will also weigh in. You don’t have to wonder. She didn’t want to go out with you and there’s nothing you could have done differently (including chasing her around!) that would have led to a different outcome.
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