OT: Relationship Advice Thread

SnowblindNYR

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Nov 16, 2011
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Just ask her out now or wait 2 months and then ask her. I never heard of asking someone out 2 months in advance. What's the difference between waiting 2 months to ask and asking now 2 months in advance? Do you think she'll reject all of the advances of other guys because she promised to go out on a date with you in January? And if she's leaving in January anyway why not ask her out now?
 
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Kane One

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Just ask her out now or wait 2 months and then ask her. I never heard of asking someone out 2 months in advance. What's the difference between waiting 2 months to ask and asking now 2 months in advance? Do you think she'll reject all of the advances of other guys because she promised to go out on a date with you in January? And if she's leaving in January anyway why not ask her out now?
Alright. But to answer the bolded, of course not, this was one of the reasons that made me think this was a stupid idea.
 
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SnowblindNYR

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Alright. But to answer the bolded, of course not, this was one of the reasons that made me think this was a stupid idea.

The point is in my opinion since she's leaving in January you can ask her now. If not, wait 2 months to ask her. Probably unlikely she'll meet someone before then. What you don't want to do is basically have her think that it's a strange thing to do and not get any benefit. I guess the benefit could be if you're just too shy to ask her for right now and she can say "let's go out now".
 
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Boris Zubov

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May 6, 2016
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There's no rule. It's a case by case basis. Anyone that tells you there's a rule doesn't know what he's talking about. This thread is full of people telling me not to date my coworker. I'm currently sitting here as we speak with my coworker. She’s now my wife.
I'm one of those guys who was telling you not to do it. And although I'm thrilled to death that it had a happy ending, I'd still give you or anyone else the same advice now or in the future. Just because it worked out for you & plenty of others, doesn't mean it can't easily go south in a hurry.

The bottom line being, it's advice, not gospel. Everyone has to do what they think is right for themselves. When I was in my 20's, I hooked up with coworkers like it was Tinder. However, back then we didn't live in today's corporate climate. If I was in the same situation in 2024, I would think long & hard about putting myself in a situation that might cost me my job.

With that said, If I knew a chick I liked was leaving, that would be an opening for me. I wouldn't wait the two months, I'd just go for it.
 

TopShelfSnipes

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May 5, 2011
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Here’s a new one: would it be crazy to ask someone out two months in advance?

I know I dismissed the “don’t shit where you eat” rule and it was definitely a mistake, however this coworker at my new place is perfect. She’s actually leaving the company the beginning of next year. 100% official. I don’t want to break that cardinal rule again, but I just want to ask her out already.

You could do it, but that also gives her two months to change her mind, meet someone else, etc. Not recommended. Assuming she's single and looking to date and says yes, she's not going to want to wait around and disqualify other people for two whole months. And even if she says yes, there's no guarantee something more immediate doesn't come along that she can go with.

Asking her out is asking for a couple hours of her time. Asking her out two months from now is asking for a couple hours of her time and two months of celibacy/exclusivity - she doesn't owe you that!

Remember: Asking her out once* isn't harrassment and any HR department will tell you that. But if she says no and you persist, that's where things get problematic.
*Assuming there are no specific company policies around that and you are not in a supervisor-subordinate work relationship.

Either ask her out now (which doesn't have to be super formal...even just a low-effort feeler like getting drinks after work), or roll the dice and ask her out in two months, but recognize that while you're waiting she might meet someone between now and then. If you wait, she also might think the timing odd. - do think about how you're going to time it and explain your interest in her. Asking her out on her known last day is going to be weird ("hey so you're leaving, wanna go out?" *winces*), as is asking her out on the first day she's not actually an employee - remember the one thing women don't respect is guys who bottle their interest up and don't have the conviction to say what they're looking for, then 'confess' later. "Hey, I was waiting until you weren't actually an employee anymore" is gonna come across weird and not saying anything but timing it that way is gonna be sus. So I'd lean towards asking her out now.

Also, I wanna advise you to slow your roll a little bit. This coworker is not "perfect" - she's interesting, intriguing, etc. and you're curious. You have no idea if she's "perfect" - that's the entire point of dating. You're asking her out because she has piqued your interest and you want to see if there might be something there that's worth pursuing. (Words bolded for impact). Don't put her on a pedestal. She's just another girl - but she's an interesting one, so you want to get to know her. She is not "perfect" nor "the one" (side note: there is no "the one" there is only "completely compatible with me" and many women will meet this criteria) - and you have to date her first to see what she's like! This is a mindset you need to have going into any and all interactions with her. Again, don't put her on a pedestal. If she does agree to go on a date with you, you're there to get to know each other...you are not there to "impress" her. I cannot stress the importance of this mindset enough.
 
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