How to have fun dating in your 30s?

I recently turned 34 and I've recently got back to dating after taking a hiatus in my mid/late 20s to focus on getting myself to a place of financial independence.

Seeing as I'm just getting back into it, I want to date different women and see what is out there without rushing into anything serious with any one person.

Problem: The vast majority of women in this age demographic (27+) all want an exclusive relationship and/or a marriage. This is further exacerbated by the fact that when they meet me, they assume I want something serious since I have my life together (I take really good care of my health, own my own house, make good money, etc).

If I'm honest with them and tell them I'm just getting back into dating and want to see what's out there before setting down, they get mad and leave. If I don't tell them and continue to see them and then after a while they ask me if we're exclusive and I say no, they also get mad and leave.

People want serious from the get-go and if you can't provide that, it's over. I want to get married by my late 30s but for now, I want to take at least the next year and date different women. Why is this such a problem for women to understand?

I remember dating in my 20s and it was so fun and you just took it a day at a time and see what evolved between the two of you. Now, it's all serious all the time. How are you all doing this whilst having fun in the process and not getting bogged down?

 

Dude I’d love to be in your shoes! People dating to be exclusive! Now a days from my experience people want to be unexclusive and seeing 30 different people at the same time.

 

I keep getting this and I don't know where you guys are finding these women! I missed out on a lot of my 20s as a result of stupid amounts of studying, working, pivoting careers, etc. I didn't date nearly as much as I wanted so now I just want to take the next several months and date a few women and not necessarily commit to one but the demographic of women I'm attracting (27+) all want an exclusive, long term relationship and/or a marriage which I understand but at the same time, all I keep hearing is how everyone just wants to hook up. 

 

I tell you cause I am in my mid twenties so maybe that’s why but I sure wish the women my age would wanna commit. Instead the women I deal with have 5 different guys they wanna go out with then you’re option B then they end up going with the shit option that’s a drug dealer etc etc. I’d love to be in your shoes where these women commit. IMO sex don’t mean squat unless there is a connection I want me a keeper🥰 I’ll quote white snake on this one “here I go again on my own. walking down the only road I’ve been living on”

 

I feel like your age bracket especially 27+ is sort of dated out at this point in time. We had the launch of tinder, bumble, and hinge all around or right after college. people could go on more dates than ever before. Even if you do that for a few years, it gets exhausting meeting, trying to care about someone new, and then growing with them. The last decade has made a mess of the dating world. I mean hell even as a guy, I am exhausted from dating. So, I completely understand if some wants something more serious in todays day than ever before. 

 
Most Helpful

Would recommend you change your mindset slightly - Word of advice from a young guy who's dated around:

Got out of a semi-long relationship in 2023 and in the first few months of 2024, dated multiple women and was having a good time. It was fun meeting people and trying new spots in the city I never did before. However, the excitement here ran off pretty quickly. Realized very quickly that casual hookups really don't make me feel anything and if I really wanted to explore places, I could just do it with my buddies who I have so much more connection with.

It gets exhausting to keep track of multiple people and their lives and another thing is, frankly many of the girls I was going out with I wasn't really into... I just sort of did it to "explore dating and meet people". But I didn't feel the strong connection I did with my ex. Realized I was doing myself a disservice and cut most of them off. This doesn't mean that I've stopped dating around, but now I'm doing 2 women max and I'm making sure that with both, there's something I can see working out long-term. Dating with intention so to say.

All that being said, I would recommend if you date, you date with the mindset of doing something longer-term and keep it a limited approach to 2 girls. It'll save you time and money. And with them, I would be upfront (not first date) but let them know you're "dating with intention". That you are interested in pursuing something longer-term but don't want to rush into a relationship with someone until you've really gotten to know them.

For my age demo, exclusivity convos typically happen around 5-6 dates from what I've seen which is around a month or two of dating? At that point, if you can look at a woman and can't see yourself committing to her exclusively, then call it quits. Don't waste your or hers time. I get the allure of dating multiple people but you need to ask yourself, what are you really even doing it for? If the end goal is to get married, then 1-2 months should be more than enough time for you to figure out if there is potential for a long-term partner.

Also word it well - don't try to come off as someone sleeping around even if at its base, that's what you're doing. Frame it as you needing deep emotional connectivity with someone before being able to give them your 100%, and you don't want to push her or you into that before you're sure. Not all women will agree with you, but think you'll get to the point where a few can see where you're coming from and will agree to keep it more casual. 

 

Thanks for the advice man!

So you went through that brief hookup phase post-breakup. Would you say you "had" to do that? Meaning, if you had just jumped right into another relationship, would you have had in the back of your mind the desire to king of let loose and see multiple women?

I think that's the issue I'm dealing with right now. A part of me feels like I need to experience what you experienced and then come to the realization that it's not what my brain perceives it to be and then seek something more meaningful with someone.

There are currently two potentials that I'm seeing, but it's still very early (two dates each) and as much as I'd like to see more women, I just don't have the time as you eluded to. But both of them want exclusivity even though it's only been a few weeks. So I can either change my mindset and pursue something more meaningful with ultimately one of these women, or forsake both and go and just keep hooking up (which isn't nearly as easy to do in your 30s).

 

RE: Did I have to do it
Current me would say no but I know for a fact, if I hadn't dated around for a bit and then come to the organic realization that it just isn't worth it, there'd be that internal struggle on if I'm missing out. Trust me I know the advice I'm giving right now is sound, but I'm not a 100% sure I would've listened to it 4 months ago if someone else told me it lol...

If you can level set and rationalize that at the end of the day, real genuine bonds take time to develop and that's what gives meaning to your life (look at friends / family) and apply that logic to dating then I feel you can get over it but if you still feel that "something" is missing, then by all means go through and date around.

RE: Your current dating life
Both of them wanting exclusivity after 2 dates is very odd to me. 2 dates is what, roughly 8 hours spent with them max (not counting sleeping over) + some texting? I don't think that's nearly enough time to be able to confidently commit to a person.

I guess I'll pose the question to you - how are your dating prospects just from an attractiveness POV? Are you able to meet lots of people or is it more limited?

 
PantherPrime

Would recommend you change your mindset slightly - Word of advice from a young guy who's dated around:

Got out of a semi-long relationship in 2023 and in the first few months of 2024, dated multiple women and was having a good time. It was fun meeting people and trying new spots in the city I never did before. However, the excitement here ran off pretty quickly. Realized very quickly that casual hookups really don't make me feel anything and if I really wanted to explore places, I could just do it with my buddies who I have so much more connection with.

It gets exhausting to keep track of multiple people and their lives and another thing is, frankly many of the girls I was going out with I wasn't really into... I just sort of did it to "explore dating and meet people". But I didn't feel the strong connection I did with my ex. Realized I was doing myself a disservice and cut most of them off. This doesn't mean that I've stopped dating around, but now I'm doing 2 women max and I'm making sure that with both, there's something I can see working out long-term. Dating with intention so to say.

All that being said, I would recommend if you date, you date with the mindset of doing something longer-term and keep it a limited approach to 2 girls. It'll save you time and money. And with them, I would be upfront (not first date) but let them know you're "dating with intention". That you are interested in pursuing something longer-term but don't want to rush into a relationship with someone until you've really gotten to know them.

For my age demo, exclusivity convos typically happen around 5-6 dates from what I've seen which is around a month or two of dating? At that point, if you can look at a woman and can't see yourself committing to her exclusively, then call it quits. Don't waste your or hers time. I get the allure of dating multiple people but you need to ask yourself, what are you really even doing it for? If the end goal is to get married, then 1-2 months should be more than enough time for you to figure out if there is potential for a long-term partner.

Also word it well - don't try to come off as someone sleeping around even if at its base, that's what you're doing. Frame it as you needing deep emotional connectivity with someone before being able to give them your 100%, and you don't want to push her or you into that before you're sure. Not all women will agree with you, but think you'll get to the point where a few can see where you're coming from and will agree to keep it more casual. 

This hits home. I'm 32 and have gone on a LOT of first dates in the last year after a 5+ year LT relationship. Granted we're talking about 30-something finance professionals so it's not so much the hit to the wallet, but it's a huge timesink and the excitement (including casual sex) wears off really quickly. Sleeping with someone is one thing, being excited to wake up next to someone is another entirely and so much harder to find. It's hard to know when the vibe will be right though (profiles and texts don't necessarily translate to real life) so I think it's a numbers game no matter what your intention is, but if something feels right, I'm of the mind to lean in instead of wondering what might be around the corner. And on the flipside, someone can be great but if you're just not seeing it, better not to waste both your and their time. 

Array
 

Not sure how you're in your 30s and are only considering 27+. The 24-27 demographic is prime territory for you. 

"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
 
wsa007

I'd love that age demographic but where do I find them? Being on the apps has been miserable.

- Spin class

- Muay Thai classes

- Church youth groups (typically 18 - 39)

- Bars

- Clubs 

"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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"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
 

Op - where are you based? I’m based in a tier three US city.  Dating in my later thirties was epic! Yes everyone I meet wants to settle and so do I! But plenty of when are willing to take it slow if you tell them why. You can say you want to settle (if that’s true), but are taking it slowly because x,y,z reason. Women who are not interested will tell you and usually be nice about it. 
 

The whole genuine and honest thing seems to work really well with the right people and many people who are not the right people. Dates are easy. Activities, walks, museum, etc. Doesn’t always have to be drinks nice restaurants etc to impress anyone.  Challenge is that many are divorced and or have kids. I was coming out of a really rough long term relationship myself where I was treated really badly. The maturity of most people really shocked me (this is good). 
 

ETA: I see you mention two women who want exclusivity. And fast. You can say that you want it but just got back to dating and want to meet people and take it slow. One thing about dating multiple women which I’ve done, it takes a ton of time, effort and memory to remember what you talked about and completely overwhelms your schedule. Something to remember. If you just want to sleep around, you can do it but there will be some tough conversations. Women also get horny so if you take it slow and they like you be ready for them to pounce on you… but know that a chat on exclusivity is coming soon…

my experience has been divorced can be more casual. They want connection but they also want to have fun. They’ve gone through the marriage dance and a lot of them have a lot of wisdom and are really open to talking about their past (which to me is fascinating). 
 

On 24-27 year olds. Plenty of lookers but man are a bunch of them clueless and is the conversation bad. YMMV, but that was my experience and I was probably like that too. It can be fun for sure but even around 27 plenty want to settle.. this is my two cents and hope it helps. To each his own! 

I used to do Asia-Pacific PE (kind of like FoF). Now I do something else but happy to try and answer questions on that stuff.
 

Definitely helps, thanks man!

I'm in Los Angeles so date activities are really easy to come by. 

I do just need to have the conversation early on, even prior to the first date it seems but I'm not expecting these women in this age demographic to stick around. The vast majority of them want exclusivity/marriage.

And yes, the immaturity of most people, irrespective of age and gender, is staggering. 

I'll look for single moms but I've seen several who are also looking for something serious on their app profiles.

And yea I can't imagine many 24 year old girls are that great at conversation, especially in today's world!

 
Jamoldo

 Challenge is that many are divorced and or have kids. I was coming out of a really rough long term relationship myself where I was treated really badly. The maturity of most people really shocked me (this is good). 

This encapsulates my dating live in Texas. Lots of great women who might be long-term fits but a surprisingly high portion of women dating in late 20s/30s are divorced with a kid. I spent my 20s on my career. It doesn't look attractive (to me personally) to start building a relationship if he responsibilities of a step father lingering in the background of most conversations. The probing questions about views on fatherhood come out pretty often and early in my experience in Texas. 

Array
 

This experience shocks me, especially being in LA. For context I just spent 2.5 years out of a long relationship and I was 28-31 in that timeframe. I dated around a ton and went from 24-33 and not one of them wanted to be exclusive that quickly. There are plenty, especially at the upper end of the spectrum (27 plus) where I spent most of my time that I think if I had asked that early they would've agreed that soon, but none of them brought it up. I will say if you have your shit together, a lot of girls will assume you are dating intentionally and not just casually so there is definitely something to that. Overall, just continue meeting girls, maybe keep a more causal vibe, and have some fun for a while. As others have said, it gets very tiring pretty quickly as the novelty of it wears off, so once you have your fill, I would be prepared to move on to 1-2 girls at a time and being more selective in who you meet/date (if you dont see a future, cut it off).

 

I'm shocked just as much as you. I don't get how everyone is finding all these casual girls whilst 99% of the women on these apps that are coming in my view in that age range all state monogamous/LTR. I wish I could trade places with you as you've lived what I want to experience. 

I do have my shit together and I'm probably giving off "long term" vibes but I don't really know how to not do that. I love suits so I wear those all the time. Maybe that's the problem? I take impeccably good care of my health/physique so I don't think that is the issue. I own a house so maybe that is causing these women to think I want to start a family or something?

I do want to have some fun with many women for a while and you're not the first to say that it's not nearly as glamorous as it seems to be but I think I need to experience that for myself to ultimately accept that as fact. Otherwise it just always feels like I'm on the outside of that looking in. I hope I do move past it quickly as I'd like to get married at some point in the next several years so I feel like I'm running out of time to do this and then pivot to find a long-term potential.

 

The deal has to work for both sides.  This seems obvious but is overlooked, not only in dating but in most things involving two parties.  Can't tell you the number of terrible investment ideas from my idiot colleagues I've had to smack down because they didn't even think about how we're going to get the other side to agree to it.

In this case, you're going on dating apps (not mentioned in the OP, but I gather from replies).  Every app is different but most of them are geared to finding a long-term relationship.  So by going on these apps, you're meeting girls who are in a mode of finding Mr. Right.  

If a girl just wants to have fun and hook up with guy she has no future with, there's a lot of places she can go.  There's an app or two for that, but often times she'll just hit the bar with her friends and if she's clicking with a dude then good for her (and him).  So by being on a relationship-centric app, she's signaling interest in something else and you're wasting both parties' time by engaging in that sort of a courtship ritual just to later tell her you weren't after that.

Suggest getting off the apps and going out in the real world and meeting people.  Especially in places where there's alcohol.

 

Great question. I'm on the same page.

The way I see it, there are two ways:

1) Indicate in your profile (I'm assuming you're using apps, otherwise you can just hit on younger girls irl) that you're looking for short-term. Apps usually let you indicate it or you can write it in your bio. This will unfortunately make your profile rating go down a lot and you'll be seeing only obese chicks with horrible attitude. But you'll be true to yourself and won't be misleading anybody.

2) You can just not bring up this conversation and whenever girls ask, answer with obscure statements, like "I'm open for anything". If they ask you directly if you're seeing someone else, you might have to lie and say "not at the moment" if you still want to clap their cheeks a bit more. Hopefully, once they discover the truth, you've clapped their cheeks enough and are ready to move on, so it won't be a big loss. So the strategy is basically to start clapping their cheeks asap and hide intentions as long as possible, so that when they discover, you're already ready to let them go.

I am personally sticking to strategy 2. But if you're a more honorable man, feel free to choose strategy 1.

 

Why are you are confused why woman do not want to do that... Put yourself in their shoes for a minute.

Say they are 30.

They date someone for 4 years to get comfy with marriage.

Engaged for 1 year

Married by 35...

But 35 + is considered a geriatric pregnancy and risks go way up each year after. So if they want kids, they are putting themselves in a potentially difficult situation if they have a relationship fall apart at any point past ~30 really. BTW my math is just for 1 kid, if they want two, then that adds even more risk for them.

Point being, yeah no shit they are apprehensive lol...

Honestly, at your age you should have a pretty good idea of what you want and do not want. It's not rocket science if you are over ~23 - 25, let alone 30+.

Above doesn't apply if you don't want kids of course, but if you do, your pool shrinks considerably year by year. Although, you can probably down down ~3 - 6 years. IE 32 dating 28 year old is nbd.

 

4 years to get comfortable with marriage is nuts.  Tip to the women - if a guy is dating you for 4 years and hasn't proposed, he likes having you around but doesn't want to marry you. 

I come from down in the valley, where mister when you're young, they bring you up to do like your daddy done
 

Not confused. I think I definitely didn't word my post correctly. What I meant to say was that dating now just doesn't feel like dating, it feels like some sort of robotic interview. You need to lay out your intentions from the very beginning and then if they don't coincide, you move on, irrespective of whether or not you really know the person. I get why they have to be like that because of the biological clock and what not, it's just removed that element of meeting someone organically, letting things unfold between you two without any contrived end goal, etc. I guess that is wishful thinking though and as others have eluded to, I should just date much younger women if I don't want to deal with this.

 

In the end you will have to find your own way. It took me forever to do that because I was going on boards AB’s asking friends and family and reading books and not being myself. I have found in my thirties that people value authenticity. You can always be chill and say “hey if that’s a problem and it’s not a for you that’s totally cool”. And actually mean it. You have a good job and are smart etc. add if you are not a total clown or jerk and treat people with respect and have actual outside interests and can have a  half decent conversation then you are better than about 90 percent of dudes. Really. 
 

go get em

I used to do Asia-Pacific PE (kind of like FoF). Now I do something else but happy to try and answer questions on that stuff.
 

If I'm honest with them and tell them I'm just getting back into dating and want to see what's out there before setting down, they get mad and leave. If I don't tell them and continue to see them and then after a while they ask me if we're exclusive and I say no, they also get mad and leave.

But what does this mean?  Why even bother dating if you aren't looking for something?  Hooking up is plenty easy if you've got your shit together.

Look at it from someone else's perspective.  They want something; a stable, committed relationship, and if they're in their late 20s/early 30s, it is perfectly reasonable to want that sooner rather than later.  So why in the world should they waste time with you, once you're open about the fact that you're not there yet and don't intend on taking steps to be there in the near future?

You want a harem of women who you can casually see, sleep with, and hook up with while explore a bit.  The problem here isn't the unrealistic or unreasonable expectations of the people you date, but yours!  You don't seem to understand what "dating" means - you want to spend a year just fucking around, which is fine, but that isn't dating.

You are taking people out under false pretenses, so no shit they're angry or walk out when they realize you have no interest in them - you ARE the bad guy in this situation.  Just hook up casually on Tinder or whatever, or go to bars and meet people, or hire an escort, or whatever, but don't go waste people's time by deliberately playing dumb and then act outraged that for some reason no one is willing to fuck you on the regular without any kind of additional commitment

 

I get what you're saying man and I definitely misworded my original post but let me clarify.

Girl I was just seeing, 31 years old.  At 2 dates she hinted at being exclusive. I wasn't exactly sure of what she meant since it was a bit vague so a day or so later, I called her to talk things out to understand what she meant and where she was coming from.

She said that she meant that for herself and that she understood that some people date a number of people at a time but for her, that wasn't her thing. She also said she understood that she doesn't expect me to abide by that, certainly not soon, that she still wanted to get to know me and go out more, and she was appreciative of the fact that I called her to talk.

12+ hours later, I get a text from her saying it was nice spending time with you over the past two dates but that we clearly want different things, peace out.

I genuinely liked this girl and I really wanted to spend more time with her and get to know her more and potentially be in a relationship with her. She was even making me consider completely dropping the whole casual thing, even just stop going on dates with other women and just focus on her for a few months but I didn't even get the chance to do that.

Some say that she had an option B guy that she went back to which would be hypocritical if she did since I take it she didn't like the idea that I might be dating other women. Who knows, point is, I feel like I did everything I could to be as respectful and accommodating to this girl and understanding where she came from and what she wanted but in the end, it still didn't work out. So back to my original post, whether or not you're honest and upfront, it seems like it's irrelevant. 

 
wsa007

She said that she meant that for herself and that she understood that some people date a number of people at a time but for her, that wasn't her thing. She also said she understood that she doesn't expect me to abide by that, certainly not soon, that she still wanted to get to know me and go out more, and she was appreciative of the fact that I called her to talk.

And did anything happen in the interim?  Something about the story seems a little suspicious, given that she's going from "yeah go ahead and date around and it's fine" to "no it isn't"

Who knows, point is, I feel like I did everything I could to be as respectful and accommodating to this girl and understanding where she came from and what she wanted but in the end, it still didn't work out. So back to my original post, whether or not you're honest and upfront, it seems like it's irrelevant. 

It seems like what happened is that this woman, who was very upfront with you about what she wanted, decided that actually she wasn't okay with you dating other people.  She thought about it more and changed her mind. What's the issue here, except that you aren't being handed everything you want on a silver platter.

Look, you need to take a reality check and get your head out of your ass.  I mean that in the nicest way possible.  You seem to have a fundamental misunderstanding about how consent and dating works.  You aren't owed anything.  This woman doesn't have to date you, she doesn't have to give you a reason, she doesn't have to be locked into whatever reason she gave you yesterday.

Your position here is that because you are upfront and honest about the fact that you intend to try and sleep with other people, that should be enough for everyone else to be okay with it.  That isn't how it works.  You know what will fix your issue?  Don't sleep with other people!  It's perfectly reasonable for anyone to have as a dealbreaker that their potential partner not be fucking other women (or men).

I genuinely liked this girl and I really wanted to spend more time with her and get to know her more and potentially be in a relationship with her. She was even making me consider completely dropping the whole casual thing, even just stop going on dates with other women and just focus on her for a few months but I didn't even get the chance to do that.

What are you talking about?  You did get the chance to do this.  You absolutely could have dated this person exclusively.  The level of entitlement here is astonishing.  You told her that you wanted to date around while you got to know her, which she initially seemed okay with but had second thoughts about.  You shot your shot and tried to have your cake and eat it too, and it backfired.  That's on you!  You're playing this "woe is me" card while completely glossing over the fact that you absolutely had the chance to "drop the whole casual thing".  You genuinely liked her, but not enough to not fuck around.

With all due respect, you obviously aren't looking for a serious relationship.  If you weren't complaining about it, I'd say it's to your credit that you're being honest with people, but you still seem to think you're owed something.  No one is obligated to give you their time or their body or their emotional attention.  You don't seem to fully grasp that, since you think it's rude of people not to bend their priorities and morals to your wishes.

 

Asking for exclusivity after just two dates is absurd and not normal. She is basically trying to lock you up and seems like a pressure tactic. Conversation should only come up after at least a month of dating or maybe 5+ dates at least. 

This girl is clearly looking for the fast track to commitment and marriage. Even if you accepted exclusivity, her next ask is going to be engagement and marriage real quick.

She is likely also seeing another guy, and you happen to be higher value then the guy she is currently seeing. But because she can't get you to commit but can get the other guy to commit, she left you for the other guy.

 

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kanon's picture
kanon
98.9
9
bolo up's picture
bolo up
98.8
10
numi's picture
numi
98.8
success
From 10 rejections to 1 dream investment banking internship

“... I believe it was the single biggest reason why I ended up with an offer...”