Associate in my mid-late twenties, my director is amazing - I just really like her. Maybe I'm telling you all because I can't tell anyone else.
Trending Content - Off Topic Forum
Career Resources
WSO Free Modeling Series - Now Open Through
May 31, 2026
9 Free Financial Modeling Lessons
Get instant access to lessons taught by experienced private equity pros and bulge bracket investment bankers including financial statement modeling, DCF, M&A, LBO, Comps and Excel Modeling.
+Bonus: Get 27 financial modeling templates in swipe file
+Bonus: Get 27 financial modeling templates in swipe file
High Finance Applications
Guaranteed
Get at least one offer GUARANTEED
- 1:1 support
- 92% success rate
- 2,000+ mentor network
- Unlimited Live bootcamps
- AI for resume + LinkedIn
- Networking automation tools
- HireVue simulation tool
- Full course library
- Private Slack community
- 20hrs of mocks
- + much more...
Two options:
Do nothing and think with your head rather than thinking with other parts of your anatomy.
Ask her out under the assumption you will be turned down, and either your career destroyed/ fired.
Really, go look elsewhere
great assessment.
I'm really interested in the self-sabotaging part of subconscious that is still down to take the risk.
This is like falling in love with a stripper. Going for her is not going to end well for you emotionally or financially.
What kind of thing are we talking about? A "#1 boss mug" , or a file someone handed you to give to her?
think more along the lines of the mug but instead of a mug an expensive ring haha
Wow! This escalated real fast!
you can flirt, but never using overtly sexual language. if you don't know how to do that, then stay away...you are not ready for the big leagues.
yeah whats the play then, just develop a good platonic work relationship and hope some day it goes somewhere? haha fml.
if you know how to flirt...you don't need to use overtly sexual language. Just the tone of your voice and basic body language can communicate everything you desire (but only if you know what you are doing...if this is your first time, then go practice on other people where there is no risk to your career). This flirting with very subtle sexual tension is what girls want anyway. After a few weeks of sexual tension,when you are at a bar grabbing drinks (its bound to happen) then you can put her in the position with the opportunity to give the green light. But, never put yourself in a position to get fired.
Facts!!!
OPs user name checks out
sure does
I never had a female director or manager so I really like this topic. Please keep us posted!
I think it is difficult to get this right. You don't want to burn the professional relationship you have. But you need some feedback from her whether she feels the same. You can use the not-overtly-sexual-flirting from above. If you both feel the same you could then decide to move to another firm to date her without restrictions. However, if your flirting attempts go wrong you might need to look for another job or another department inside the company anyway. All in all, if you decide to turn thoughts into actions it quickly turns into a question of where you want to work. My two cents.
Isn't she way older than you? I've dated chicks older than me a few times and it doesn't really work because they are on a clock. There's no real winning for you in this case though.
She is relatively young for her position, she is about 8 years older than me. Yeah there is no right move, anything remotely direct will get me fired if it's not on.
this is stupid. if you are late 20s and she is 8y older, she has only a couple of years max before she needs to seriously think about kids if she wants them
username checks out
Rub one out and reassess
Post nut clarity, best time to make a decision.
If you're still into her after this... RIP my friend you are in love
I like how this is “most helpful” as opposed to “funniest”
This might be my highest rated post ever
Edit: Got to +100
Well your advice is spot on actually--often times men conflate horniness with love when they're with a girl....better to rub one out and THEN see if it is love in fact
Honesty pays off.
well deserved
You should honestly dod that before 80% of big life decisions lol
+1 SB. Not actually giving you a SB tho bc I don't want to be responsible for knocking it out of 69
.
What do you have to offer her that she cant get from a thousand older, richer dudes?
why would the richer dudes be chasing someone on the wrong end of 30 when they could be going for mid twenties etc?
nothing
youth. she will be a middle aged woman with a guy in his early thirties
What he has to offer that she can't get from a thousand older: 1st: younger scooby (his genitals) 2nd: brains if he can seduce her 3rd: she won't throw up every time after having sex with him
Oh ... this counts more than monies :)
Dude grow a pair of nuts and just leave em hanging. If she bites, you know what to do. Otherwise, this is just sad.
what?
under no circumstances should you ask out your superior, ever. no only will she most likely say no, she could be fired if she pursues anything, and unless you look like david beckham with an eggplant appendage, you're not worth it.
if she gets assigned to a new group where you're not subordinate to her, yeah see how it goes at a work happy hour, but otherwise forget it dude.
This is the right answer. Not only is she unlikely to be interested, but she would almost definitely get fired for hooking up with a direct report. At the very least one of you would have to switch groups
Yeah, imo someone else here nailed it.
Continue to talk to her in a somewhat flirty way, if you ever decide to move jobs thats your chance to move forward with it
You know, when i first got into industry, I thought... hell, no big deal but after years gone by, I've realized how small the industry was and the last thing I've ever wanted to do was burn bridges even when I was in back ops at the time. Yeah it was back ops, no big deal, right? No way... if an MD doesn't like you, you're fucked. But, I can't say I haven't. Well, she was a VP for JPM in Jersey City. I knew i would never work with her so hell, I went for it and I was an analyst at the time lol.
Whatever you do, make sure you start visiting hr and document that a superior is making advances and you feel it might get uncomfortable. Don't mention specifics.
Slowly work her up to a crescendo and if she really lays the hammer down go to HR and say it's retribution for spurning her advances.
This my friend is what we call a win-win-win.
Daaang
Cold as ice Charlie Murphy
Hahaha funny as fuck
If you pursuit her , prepare to say goodbye to your career in banking. Also since when did WSO become a romance consultation center?Thats what the app hinge and website eharmony are made for.
maybe the reason why everybody wants to go into private equity is so they aren't in banking anymore and can date their bosses
ask her out via text message
It is absolutely OK to express your feelings for her. After all, if you have a thang for someone, that someone needs to know right?
Does she have kids? In that case be prepared to be a father. I truly believe it is a plus if you manage to hook up with her - reviews gonna be positive from here on.
If she hired you, probably you have a chance. (Hey, she liked you so you got the green light) If not, don't bother. Too much downside and too much risk. (You are on this site, no need to explain that further right?) Upside? Knowing that she's in the late 30s and still single. You go figure. (Yeah, the rare gem you say)
Loving someone is easy, staying faithful and not getting tired is hard. Let the passion sink in a bit and design a game plan before you make the stupid move without a plan.
I feel like the answer is so simple...exit to PE/HF asap to get the money/drugs/girls...and lose the HR liability..., then tell her you love her...
The methodology to approaching this should be the same as it would be with any girl you’re truly interested in, though the outcome may be different.
Based on these questions it’s easy to see that your situation makes this a risky play, but that doesn’t necessarily mean it’s not worth it to you. Size it up - make a call.
Question no one is asking... does she like you?
It all depends on the relationship between you. If you are just working together, then go find someone else. If you have some kind of friendship, you can try, but be careful
Don't shit where you eat
Oldie but goodie. OP did not say much but it's likely that he is making a fantasy out of this director he finds attractive, professional, etc.
Are you sure it's not a symptom of decent looks + proximity? Or are are you a lazy fuck that doesn't like approaching real women outside of your immediate obligations like work/school?
First find a job eslewhere. Then tell her you've always liked her but didn't want to make it weird while working with her. You'll score a lot of points.
However not sure if you like her to the point of changing your job...
Just get Tinder/Bumble/Happn/The Inner Circle and your problems are solved. There really is no excuse to be a dateless wonder these days when finding someone is literally at your fingertips.
Honestly, I'm a 4/10 and tinder gets me 5+ dates a week. Just click some buttons on your phone and bam now you have a girl
If you could get with a girl worth 10x plus your net worth, you wouldn’t be fantasizing about a woman 8 years older than you.
Move on man.
This is interesting. Do you think you two have some chemistry in the works? What's her body language like around you? I know of two associates at MM bank in the same group, that started dating secretly then actually ended up getting married. Still work together last I heard.
Conversely, have a close friend who had a fling with his boss/direct report (non-finance); when he ultimately broke it off with her, his work life became a total nightmare and had to switch jobs over it and to get out of the toxic situation. Just food for thought.
Flirt VERY conservatively (like barely even flirting) so as to not risk your position, wait until you exit, keep in touch under professional pretenses, and eventually make the move if you get positive feedback
It is suggested to stay.
Oh MD you. You got what I neeeed! But you say I'm just an associate, but you say I'm jut an associate!
+SB for Biz Markie, the relationship rapper. :)
This is awesome. Well deserved SB
She's a Banker Chick.
Just Say No.
Good things come those who wait
It largely depends on the sort of person she is, you'd want to be careful not to do anything implicating.
any updates?
@sadsoul90" please give us an update? did u smash?
I took CRE's advice, cant ignore 100 SBs.
Better yet, I would've had sex with her and then reassessed
Dolores velit qui dolores quia aliquam dolor qui. Accusantium qui at dolores facilis. Dolore nulla delectus soluta soluta nihil. Culpa sint aut quam consequatur atque. Est voluptatem porro provident et optio numquam eveniet veniam. Est rerum corrupti sit commodi quis.
Tempora dolores esse recusandae minus quibusdam. Est accusamus quis adipisci saepe dicta tenetur.
Porro necessitatibus dolorem iusto pariatur laboriosam. Sed ut eligendi quidem fuga.
See All Comments - 100% Free
WSO depends on everyone being able to pitch in when they know something. Unlock with your email and get bonus: 6 financial modeling lessons free ($199 value)
or Unlock with your social account...
Non dolore aut quasi aliquam totam recusandae. Provident sunt est iste itaque. Consequatur eum neque reiciendis quidem blanditiis reprehenderit alias. Accusamus quia dolorum aliquam vitae molestias officia voluptatem. Id ut nulla eos quo corrupti voluptates.
Velit reprehenderit at at distinctio perspiciatis adipisci. Placeat quo non corrupti quo dignissimos asperiores laudantium non.
Sunt nobis qui fugiat perferendis esse. Mollitia qui repellat ratione et libero est.
Et facere neque qui consectetur tempora eos sit. Dolores cum earum praesentium nulla numquam.
Est sed id in corporis velit. Quia odit possimus dolorum est sequi. Sit et libero sint illo accusantium. Omnis voluptates sint ut voluptatum. Sint doloremque dolores sit numquam molestiae quo.
Sit velit voluptatem facere non numquam. Et est et qui excepturi. Commodi nihil ut est nobis fugiat. Animi officia necessitatibus consequatur laboriosam sunt ut. Ut in animi non id eos.
Assumenda aut quasi facere consectetur ducimus facilis qui. Rem odit rem assumenda ad a. Sit et et animi facilis. Debitis commodi unde autem et aut qui.