How to avoid grass is greener mentality in relationships?

Never thought that i'd be asking a relationship question on this site like so any others, but here goes. Currently casually seeing a few girls, all of which I can see myself potentially settling down with tbh, meaning they check the boxes from a personality/character/career perspective. However, it's been tough to commit to any of them due to none of them standing out as "the one" and my FOMO over potentially meeting "the one" around the corner. For so many of us Type A-ers that adopt a grass is greener mentality to our careers (exiting IB for PE, exiting PE for HF, exiting HF for a better HF), how do you avoid that in your romantic lives, especially in a city like NYC where the dating pool is so deep? I.e. how do you feel content with your current partner when you come across a hotter woman / better fit / more attractive in other areas / etc expressing interest? Any advice would be appreciated.

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Comments (46)

Most Helpful
Sep 5, 2021 - 11:57am

Get off the dating apps. They are a plague; they are a cancer to your soul. You'll never be happy with any woman so long as you can whip out your phone and start talking to other women.


  • 10
Sep 8, 2021 - 3:33pm

This is very good advice. Dating apps are great for meeting women easily, if you are looking for something casual, or if you want a nice self esteem boost (assuming you are good looking and know how to build a profile)

But for relationships if you get sucked in they can be awful. You will NEVER find a woman that checks every single box, and if you see a flaw it becomes very easy to just move on to the next one. And once you can date so many the tiniest things become deal breakers. Instead of 'are we aligned on kids, finances, get along ok' it's 'well she makes good money but not as much as X girl I dated' or 'I like to play Tennis alot and she is awful at it... unlike Y girl who used to be fun' .... or 'we both are moderate politically but she believes in gun control and I dont'.... etc. etc. Then as you keep dating more girls and reuse the same dates (hey if it works it works) you realize dating loses all 'magic' it once had. You get their stories confused, you dont have a special memory doing something like putt putt with her because you've done that date 6x times already, etc. and literally nothing moves the needle.

Get into a relationship? Great! But after a few months when it's no longer magical but still nice you wonder 'shouldnt it be magical all the time?' and 'is it normal for me to be checking out that other girl at work if Im in a relationship? Gosh I want to be single'. We were raised thinking relationships were some disney fairy tale that that Ms. or Mr. right will be perfect for us, when in reality our parents, their parents, and their parents just got married young to one of the first 3 guys/gals they dated and then made it work (or didnt). When you rotate through a lot of women it REALLY harms your ability to form meaningful connections

  • VP in IB-M&A
Sep 8, 2021 - 8:54pm

On the other hand, this scenario happens because apps are full of mediocre options. Endless strings of average, uninspiring options with each girl having maybe one or two differentiating attributes. That is why you think back on how one did this or the other did that because, let's be honest, the vast majority of them are pretty interchangeable. 

You'll eventually meet one that is multi-dimensional but it just takes time. They are out there though so you shouldn't settle for "the best one so far" if you aren't fully convinced. That never works out, trust me

  • Intern in IB-M&A
Sep 5, 2021 - 12:29pm

Keep shopping until you find an offer you can't beat, that's what women do.

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Sep 5, 2021 - 12:31pm

depends how old you are. 

you won't hit your sexual market value until around 34 as a male. you might want to wait until then to maximise your chances.

  • 1
  • PM in HF - Other
Sep 5, 2021 - 2:10pm

Your quant research on the male/female dynamic is wayyy off my friend. 
Easy data point, this forum is full of virginity posts for incoming analysts.

OP, if you are under 27. Just enjoy life man then one day one of these ladies will crush you and grass wont feel greener and then youll meet the right one. Its a mental state.

Sep 5, 2021 - 3:16pm

there's always going to be a hotter girl.
there's always going to be a hotter guy trying to get her too.

my personal choice is to have a relationship of equals (not interested in a trophy wife or stay-at-home mum) so imo, the goal is to find someone who makes you better, you make them better, and you connect on a much deeper level where it doesn't make sense to lose all of that just for one f*ck. 

  • Prospect in Consulting
Sep 5, 2021 - 4:56pm

Well, one way is to understand that expectations and reality hardly ever align. The thing to keep in mind about dating in particular, there is no perfect partner or "the one". A relationship, in  essence, are two people who are compatible with one another willing to compromise and work on the relationship through good and bad times. You reference many other individuals being "better", but I would argue that surface level attraction is just that. They may not know nor care to know about your hobbies or interests, they may not understand nor accept that you prioritize your work over other aspects of your life, and they also may demand/insinuate that you spend more time with them. In a long-term, committed relationship, both individuals are often accepting or understanding of the others' faults or quirks and finding someone else who feels the same way on a deeper level is difficult. 

Although at the surface, every person you come across may seem ideal to date, there is such a thing as deeper incompatibility if you two don't share the same views as where you would live, when you would settle down, or compromise on how time is spent, then you would ultimately be burning your current current lawn for plastic grass that simply appears greener. An old by cheesy quote to end on, "the grass will always be greener where you routinely water it." Instead of hopping to fence to greener grass that may not even exist, it's better to create green grass where you are. 

  • Incoming Analyst in IB - Cov
Sep 5, 2021 - 7:00pm

I'd love to meet someone who is type B. Do they exist? No one ever self ID's as type B because type A is nebulous and includes nearly every positive professional trait. Type B might as well be the Dude from the Big Lebowski. 

  • Intern in PE - LBOs
Sep 6, 2021 - 12:10am

As the post right above this one on WSO says, "could you imagine your dream girl". If this one doesn't fully match, dump her.

Sep 6, 2021 - 9:35am

I saw a meme or a screenshot of a Tweet where some dude created a fake profile with his gf's photos and that profile had something like 2,300 likes in 6 hours.

If you find a girl that is attractive (to you, she doesn't have to be Margot fucking Robbie), has a good head on her shoulders, is nice, cares for you, you two click sex-wise, and she has a similar vision of life, just marry the girl. I guarantee if you don't, there are minimum 2,300 other guys who would in your place. And they will.

And then you will just be sad and alone, with someone who might be a) hot but terrible or b) great but you aren't attracted to. 

  • 4
Sep 6, 2021 - 9:16pm

It most certainly did. I guess Patrick and Andy are looking for some Chinese investment... That's saddening. 


  • 1
Sep 7, 2021 - 3:24pm

1. I'd say figure out what you want. Its okay with whatever the answer is, just know what it is. Do you want someone you're really compatible with, do you want someone who is just arm candy, or smart, or funny, or family orientated. It doesn't have to be one thing, but I would in some way come up with a "ranking" system. For example, I always think of when billionaires have wives/gfs 50 years their junior, it works because the billionaire wants arm candy the wive/gf just wants someone with a lot of money. 

1a. Figure out what you want in terms of your life. If you want a family or dont want one, ether is cool. Don't lead people on one way or the other. If you want a family though I'd say you'll prob have to leave the party before the music stops in a sense. 

2. Realize you can to pick and can't "have it all" essentially or reject someone for one thing. Yes, we would probably all want someone who is wildly attractive, wealthy, smart, gets our jokes and the like, but probably little chance of finding someone who fits that exactly. Its like a job posting, this is what we're looking for, but based on the salary and benefits we provide this is what we will get. 

3. They're that old Katt Wiliams bit about girls dumping dudes who are 98% for some guy thats only 2% of what they want. I'm not saying date a slug, but if you're looking to figure it out realize that there will always be someone hotter or prettier or funnier on a dating app, but that might just be one thing and not the whole package. 

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  • 2
  • 1
Sep 9, 2021 - 2:05am

Your issue starts with dating multiple women. You can casually see multiple women but if you're going to date then get the fuck over your commitment issues and date one. If you don't like her then break up and move on to someone else. Dating multiple women can seem appealing at first but if you're not a shitty person, you'll feel some apprehension/guilt as you don't want to lead on these girls to nothing and it just creates unneeded chaos in your life with regards to juggling schedules / working with all the feels from all parties involved. 

Step up and just focus on actually dating one woman at a time (again, separate from hooking up with multiple chicks)

  • 2
  • Investment Analyst in RE - Comm
Sep 9, 2021 - 10:13pm

Where I'm from, "dating" means "going on dates with," i.e. casually seeing / hooking up with

  • Associate 1 in HF - Other
Sep 9, 2021 - 2:31am

Start out with a roster. 3-4 at any given time. Churn out the bad, retain the good ones.

Keep recruiting and vetting and the right one will emerge.

Don't do monogamous relationship from the beginning and you will be fine, because you'll either have onenitis or feel that you're settling. 

Sep 9, 2021 - 9:33pm

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