How much trouble can you get in for asking out another analyst?

I just started in buyside AM. I have a bit of a crush on one of the other analysts. I am 50/50 on whether she is interested back or is just being friendly. I am thinking of asking her out, something casual like dinner / drinks but I am worried about blowback. 

My firm is pretty woke so I am worried I could get fired or something if she takes it the wrong way. I read the employee handbook and it says relationships between coworkers are allowed, but nothing about asking someone out. Am I overthinking this? Has anyone asked out another analyst and gotten shot down?

71 Comments
 

I agree with the first comment - don't do it. 

however, I think if you guys are the same level, it's not a huge deal legally speaking (those rules are typically in place to prevent relationships from occurring in the context of power dynamics at play, like manager and direct report)

but just don't do it, if things don't work out, it will be very awkward

 
jimbianco315

Are you 12? It might be awkward for like a week.

Or ruin your life. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Hooking up with and/or dating someone, and then afterwards being able to treat them normally, is an underrated skill

If you end up dating someone and then things go south, seeing them in the office all the time SUCKS regardless of your maturity level

and it SUCKS MORE when they end up dating someone else at work

 

My view is the (1) never date on the same team or desk, but (2) the workplace can be a great place to get to know someone as a friend and sus out if you might really like them longer term.

 

This is true. Don’t do it unless you’re actually interested in a relationship. If you just want to get laid - that will def end badly and awkwardly.

 

I get what you are trying to say but you said it yourself. That was 30-45 years ago. These days even asking once in the workplace is not allowed. By no means am I woke but that is just the way it is today.

If OP is willing to risk his employment, by all means, go for it. I have seen too many people get HR'ed for asking once or HR'ed after things fall apart. By the way, I would argue that are way more ways to meet girls in 2024 than back in the 80s so not sure why anyone would take this risk.

The saying "don't shit where you eat" has been around for decades so apparently even previous generations knew it was a bad idea. 

 
Risk Weighted Ass

In the 80's, 40% of people met their spouse in the workplace. Don't let woke people stop you from satisfying the most important part of your life. Just ask once "want to get some drinks this week?" and if its anything apart from a 'yes!' then never ask or try again. Asking once is allowed, twice is harassment.

I think you forget to realize that girls are crazy and things might be going well initially and could fall apart and she could take it out on him at work or call the police and make up charges. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
Isaiah_53_5 💎🙌💎🙌💎
Risk Weighted Ass

In the 80's, 40% of people met their spouse in the workplace. Don't let woke people stop you from satisfying the most important part of your life. Just ask once "want to get some drinks this week?" and if its anything apart from a 'yes!' then never ask or try again. Asking once is allowed, twice is harassment.

Expand

I think you forget to realize that girls are crazy and things might be going well initially and could fall apart and she could take it out on him at work or call the police and make up charges. 

Sounds like something you’ve experienced or seen before?? If so, what happened?

 
Controversial
amonkeywso
Isaiah_53_5 💎🙌💎🙌💎
Risk Weighted Ass

In the 80's, 40% of people met their spouse in the workplace. Don't let woke people stop you from satisfying the most important part of your life. Just ask once "want to get some drinks this week?" and if its anything apart from a 'yes!' then never ask or try again. Asking once is allowed, twice is harassment.

Expand

I think you forget to realize that girls are crazy and things might be going well initially and could fall apart and she could take it out on him at work or call the police and make up charges. 

Expand

Sounds like something you’ve experienced or seen before?? If so, what happened?

It wasn’t at work, but was seeing this girl in NYC and was over it and stopped hanging out with her and she lost it and filed fake charges with the NYPD saying I harassed her on the phone 5x per day for 3 weeks. I was arrested immediately for a misdemeanor charge.

Turns out phone records showed that I called her zero times at all that whole month and the case was thrown out eventually, but it took 6 months of court dates to resolve (court 1x / mo) and she never showed up to court once, but I had to be there or would get arrested. I tried to talk to the prosecution to press charges against her for perjury, but the prosecution didn’t want to press charges and she got away scot-free.

My mentor in my first job warned me to never fish off the company dock, and I never did. But, my experience with her showed me how evil girls can be if they feel like they aren’t getting the attention they deserve.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

If you’re 50/50 she’s probably into you. Do it, but in a casual way like asking her to a social event or a simple coffee and go from there. 

 

Not an HR issue. They only care if you go on a date with your manager or something along those lines where it would be non-kosher with reporting lines. Analyst dating another analyst is maybe not personally advisable, but HR would be fine with it.

I would ask her for lunch first so you can try and get more of a read on whether she's interested. Lower risk and totally normal for coworkers to get lunch. Then drinks if that goes well

 

Spend more time at the office first - chatting, lunch, grabbing a coffee - wait until you have greater certainty that she 1) likes you, 2) you definitely like her, and 3) she is stable and is not going to report you or get really dramatic on you.  A work romance is also a huge distraction and time stealer.

Beyond the current era's concerns about HR (which are significant), dating a coworker and having things go south, sour, weird, etc. can be extremely awkward, uncomfortable, miserable, etc.  This is somewhere you are spending a LOT of hours, are under scrutiny and need to perform, and these relationships rarely last. Even if you make an agreement not to be weird if things don't work out, well, it will likely be unpleasant. Especially if one of you moves on to someone else at the office!  

I don't know many people who met their spouse at work, but I've seen a LOT of REALLY bad blood between at-work paramours who have fallen out...it's a lot more entertaining for those watching than those experiencing it.  It's definitely risking train wreck-level drama where you work.  So really, unless this becomes more than a crush and it's mutual, dating a coworker is potentially asking for a lot of aggravation.  

Leah R. Matsil
 

Not a management/HR issue, more a personal issue - coping with a jilted, unhappy coworker, at close range, on a daily basis, which is distracting, wastes time, awkward, uncomfortable, and everyone in the vicinity senses it.  This person may start talking about the details to colleagues, etc.  

Leah R. Matsil
 

Just be respectful, acknowledge that it could make her feel uncomfortable and it’s not your intention. “If you’d ever like to get a drink outside of work let me know, I’d really like that”. Don’t make her have to answer on the spot as more likely to make her uncomfortable, just let her know explicitly you’re keen and leave ball in her court. If she doesn’t follow up etc then she’s not interested and you were categorically not disrespectful.

 

Probably not worth the risk, unless truly worth the risk. Look outside, there are plenty. If still truly interest in her, reassess. Some have given a couple of good approaches above. The fact that there is no power relation helps, but still nowadays you never know. Once you make a move you set in motion gears that you may not fully understand or control. It may be the best decision in life or a fateful one. So again, it should definitely worth the risk, and play it eq and iq wisely.

 

I would do it, but don't make it seem like a date, and then gauge her reaction, etc. Once you guys are together outside the office and have had a few drinks it should be pretty clear. 

I recently did this with a coworker from another office and it worked out. Just try and give yourself some plausible deniability.

 

Have navigated this office situation a few times.  My experience (whether it's an office girl or not . . but applies especially well to the office) is that you never lose ground by casually getting to know someone in a friend/acquaintance context. People will tell you that you could get "friend zoned" but in reality I've never seen a guy lose ground because he became a friend. I suspect the mythical friend zone is a cope invented by unattractive men and sympathetic women to pass off the guy's failure as a tactical error.

That advice applies everywhere, but especially in the office because it buys you time to feel her out without the tension of asking out a coworker in a firm that might be weird about it.  

 

As the girl.. one office coffee and a few casual HH drinks later and 2+ years of dating because he had the balls to ask. Just don't be weird. 

 

love how there's no bananas given to you as maybe the only female commenter on this topic
you're probably the only person who should be listened to here!

 

It can work, but a lot of guys aren't good with shooting their shot at women and come across as weird, and sometimes women are the weird and awkward ones. It's easy for a woman to say "Don't be weird." Women are sometimes blind to the reality of a man. Many men have to learn how to court women because it doesn't come naturally to them, but women have the luxury of sitting back and waiting for the right guy who knows how to talk to women and not be weird to come to her with very little risk. Oftentimes the guy who hit on you that wasn't weird has had many awkward rejections, humiliating experiences, and learned from a lot of trial and error before he got to you. The risks of learning that in the workplace are uncomfortably high.

And as most men eventually figure out, a woman's threshold for weirdness rises the better looking a man gets. The loser who has no friends and eats lunch by himself every day starts becoming more "mysterious" the hotter he gets. Women start making more excuses for asshole and douchebag behavior the taller and more handsome he becomes, and the weird shit he says and does starts becoming cute and adorable the more she and other women find him attractive. The workplace can be a dangerous place to test out how hot women think you are.

I don't know this guy though. For all I know he's a pimp.

 

This can definitely be navigated if you play it with baby steps.

Start with starting up conversations with her on a regular basis and see if she is receptive and if she initiates back as well.

If that goes well then move on to seeing if she wants to do lunches or happy hours with you and a group. If she is receptive and initiatives back then you move on some more.

Then it’s lunch or coffee with just you. Again if she goes along and especially if she initiates back - then you’re on to something.

Then at this point you can ask her to go out with just you and maybe some of your friends, no work colleagues. Again if she’s into it - you’re getting there. And if not you still haven’t exactly crossed the line by asking her out on what can be considered a date. You’re still in the friend zone so it’s not really awkward if she pumps the brakes.

By the time you get to this point it isn’t 50/50 - it’s like 95/5. If she def wasn’t interested she’d not have gone along with all of the baby steps.

“Don’t shit where you eat” is the safe strategy bc if it doesn’t go well - you don’t have to see her.

But maybe it does go well and then maybe that’s the person for you. No risk no reward.

But you cannot get fired for going about it the way I described above.

 
Monaco Man

"How much trouble can you get in"

Well, depending on your rizz level (assuming you have zero because of your role) - you could get fired

You are forgetting the latter end of the equation. He could have good rizz and get into the relationship just fine. Getting out of the relationship is when things go awry.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

You're crazy for considering this, and you guys are crazy for encouraging this guy to even consider this in a post #metoo world. There are so many ways this can go wrong and the consequences, if it does, borders on complete career suicide to jail time. You're not just risking a little damage to your reputation these days. It's really not worth it. I get it you're a man spending a lot of time with the women at work, it's natural to develop feelings. People typically develop some type of feelings for one of the people they see every day like work, social groups, classes, clubs, school, teams, etc.

What if you shoot your shot and miss and she doesn't take it well, and she is the one being awkward about it? Her discomfort can easily lead to a call to H.R.

What if she likes you now and you have a bad date? See above.

What if you have a few good dates, hit it, and it's a bad fuck and now she's being awkward about it. See above.

What if you have a relationship and a bad breakup? See above.

What if some asshole sees that you hit it and thinks she's easy, starts talking, now the office is talking, and now she's mad. See above.

What if other girls find out that you're hitting it and now they think she's the office ho and she gets embarrassed, doesn't know how to handle it, and throws you under the bus to salvage her reputation? See above.

What if she regrets it for any reason? See above.

What if some simp that also likes her starts hating and causes you trouble?

What if some girl that's hating sees it and causes you trouble?

What if she starts running her mouth to people in the office and rumors start spreading that get out of hand and now you're in trouble?

What if you shoot your shot, miss, and she tells other people who start looking at you funny and now you're the office creep and some other girl reports you to H.R.?

And what if you live happily ever after like it's a Hollywood movie?

I've seen all the scenarios I've listed play out in my lifetime and the consequences are too high for a man to gamble his career/life/freedom on a woman at work these days. You're putting your life at the mercy of her emotions and other people's emotions that you can't control. Like other people said, there are just too many other ways to meet women these days than at work, and even our grandparents warned us about it way before #metoo popped off.

I even did it one time, and she ran her mouth to everyone at work the next day, rumors started spreading, dudes started hating, other dudes tried hitting it because I did, and she got mad, and this was before #metoo. That nut wasn't worth the drama that came with it.

Relationships are messy and they're always a risk. The stuff I mentioned happens in all types of relationships but when you start mixing them with your career and livelihood and with someone you have to see and professionally interact with every day in a controlled strictly professional environment no matter how it goes, especially in a #metoo believe all women no matter what culture. Just an accusation alone can get you in a world of trouble, and the accusation doesn't even have to come from her. You're playing with fire. It's always easier to get rid of you than to find out your side of the story or the truth. All the company cares about is avoiding any liability and keeping the office focused and productive. An office distracted by high school drama isn't focused and is getting too close to liability. And sometimes a great partner doesn't always make a great co-worker. Just cause you can date someone doesn't mean you can work with them every day.

For the most part, work is about making money, not finding love and making friendships. Yeah, there are exceptions, but for every positive story about people finding their spouses and best lifelong friends at work, there are dozens of stories where things went left. So use your common sense, and logic, and proceed with caution.

As a side note, it's easy to figure out if a girl likes you after some experience. It can range from straight telling you (which is a masculine trait and a possible red flag for anything more than a good time but not always), to always finding reasons to be around you and talking to you. Girls typically make it easy when they like a guy. They'll go out of their way to make sure you have idle time together, they'll make themselves easy to approach with no friends around, they'll seem to always have free time, they'll always be bumping into you, they text back right away, won't flake, etc. Usually, if there's any doubt it means your intuition is telling you she's not feeling you like that. If she's making it too difficult then she's not feeling you like that either, and if she's throwing too many mixed signals then she isn't either.

The way women typically shoot their shot is by making themselves easily accessible, and available, and presenting themselves to you in the best way possible. I said for you, meaning if there are too many coincidences. She probably doesn't share all your hobbies, she probably doesn't like the same sports teams and restaurants, and your jokes aren't that funny. But magically she is always free for you, likes the same shitty team as you, loves everything you like, starts wearing your favorite color, and you're the funniest man alive and you start thinking she's the most perfect woman on Earth. One or two coincidences can be normal, but too many are deliberate and a red flag. You probably wouldn't want to date yourself either.

The problem with hitting on women at work (whether you work there or not) is she has to be nice to you for the most part which can send the wrong signals and make it awkward and uncomfortable for her when she doesn't like you and you're not catching on. It's typically a bad idea to hit on a woman at work unless she is displaying some really clear choosing signals, and even then it can go wrong with some of the above scenarios. Chances are she's just being friendly to a co-worker.

With all that said, there is a possibility that I'm full of shit, you shoot your shot, everything goes amazing, you get married, 2 kids, a house, and live happily ever after and she was worth risking it all for, or you manage to have a small fling with no major consequences. But things like this don't typically work out that smoothly. Just proceed with caution and keep in mind all the ways this can go left on you which you don't have control over.

 

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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

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