How do you become a ‘fun guy’?

My fiancé keeps saying I'm too serious and boring. We share different interests in what we consider fun, but I'm willing to conform to her interests as it'll make her feel good. However, I can't force myself to be fun, it just needs to happen. Anything I can do to come out of my shell in that regard? It kind of makes me feel bad, tbh - I always hear it.

Comments (87)

Oct 29, 2020 - 8:39am


nything I can do to come out of my shell in that regard? 


just trying to live like Hunter S Thompson

  • 13
Oct 29, 2020 - 8:54am

Why is she with you if she finds you boring? Is it a case of you were both young and had similar interests and have kind of split in that sense since or have you always been boring?

It seems quite odd she would be with someone she finds boring.. And that you both would want to get married to each other despite not having interests in common

Oct 29, 2020 - 9:18am

She is actually socially anxious unless she's with her friends or ppl she's familiar with. She likes malls, restaurants and anything related to the typical way of having fun. I like outdoor stuff, renting a U-Haul with a friend and just driving nowhere while sleeping in the back and stuff. Basically very unconventional things. I want to conform to her needs as that's what relationships are about and I'm not gonna make her do the things i like doing.

Oct 29, 2020 - 9:29am

I want to conform to her needs as that's what relationships are about and I'm not gonna make her do the things i like doing.

I don't know if you meant to come off this way, but this sounds kind of one sided. Yes you gotta do somethings she likes, but so does she, no? 

The main thing about money, Bud, is that it makes you do things you don't want to do.

  • 2
Oct 29, 2020 - 9:37am

You sound more "fun" than your fiancee tbh. Most women crave spontaneity so kind of sounds like she's on the "Karen" track of vanilla. Just know that her degradation of your character will intensify if you marry her (marrying a woman unleashes any negative traits she has been suppressing as she feels she has you where she wants you now), so I would consider getting someone that "builds me up" versus the alternative.

If you're not talking to her/her friends you probably find what they want to talk about boring and unfulfilling. Again, this isn't anything to do with you being "boring". You probably just like talking about shit that matters.
Im not going to say thats so atypical for a guy. A lot of women are like squawking seagulls if you listen to them talk about the Kardashians or some stupid shit. Its best to check out in those moments.

But again, most women would love some spontaneity/romance in their life, going off and seeing some new and exciting place in an unconventional way. If you enjoy that you might want to find someone else.

With all of this being said, if you're not an abusive drunk of raging alcoholic and you want to be "fun", alcohol is a great social lubricant. I'm a bit of a social butterfly generally but if you give me alcohol it's like giving Popeye spinach. Your "fun" factor goes up tremendously when drinking, especially if everyone's drinking they think you're funny instead of annoying generally.

  • Associate 2 in IB-M&A
Oct 29, 2020 - 4:50pm

Friend of mine was in a similar relationship where there was misalignment of the things they really enjoyed. He would go out of his way to do the things she liked but there was no reciprocity. They had a really great relationship but after 4 years of being together he realized she was never going to be willing to put forth the same effort to try and enjoy what he liked, he had to end the relationship and is now much happier for it. Not saying your relationship is the same but the resentment will set in eventually if she isn't willing to put forth the same effort.

Oct 30, 2020 - 3:26pm

Man I was gonna get on you and tell you try try out some a few sports and outdoorsy stuff like surfing/biking but she definitely is the boring one. Nothing wrong with having different interests, most of the girls I've dated aren't into outdoorsy stuff like me but understanding you need a day away from each other everyother week to do your own things is super important. Also she shouldn't be putting you down like that. Might be time to have a frank conversation

Oct 29, 2020 - 9:32am

Its the old Katt Williams skit where girls will break up with a guy who is 98% of what they want bc they can't have the other 2%. 


Idk, this always seems like a tricky situation. On one hand, you're engaged, but on the other hand, if she's complaining now that you're not fun, its hard to see that getting better unless you change yourself; but if you have to change yourself to be with someone, that might not be a fit. 


I'd say maybe try to find one thing she deems "fun" and then try to enjoy that and do it with her. 

Oct 29, 2020 - 8:54am

Unironically start casually doing drugs. Not like crack or meth obviously but experiment with weed, lsd, mdma, coke, etc. I particularly recommend the first two but for lsd do your research and stay away if you have bad anxiety. And be wary of the others if you have an addictive personality, ESPECIALLY when it comes to pills.

This is gonna sound kinda cringe but getting into weed n drugs n shit as a teenager led me to meet so many different people and experience all sorts of environments. I guess I got lucky with my work ethic/discipline and it never messed me up or took me off track (as it does for some).

Other than that, I'd suggest that you start just getting out of the house and doing bullshit. Day drink and go to an art museum, bet money on street fights, climb random buildings.

Oct 29, 2020 - 11:22am

Try to act like Kawhi Leonard

I’m a fun guy. Obviously I love the game of basketball. I mean there’s more questions you have to ask me in order for me to tell you about myself. I'm not just gonna give you a whole spill... I mean, I don't even know where you're sitting at
  • 8
Oct 29, 2020 - 12:41pm


My fiancé keeps saying I'm too serious and boring. We share different interests in what we consider fun, but I'm willing to conform to her interests as it'll make her feel good.

Danger, Will Robinson.

"Son, life is hard. But it's harder if you're stupid." - my dad
Oct 30, 2020 - 9:28am

Layne Staley


My fiancé keeps saying I'm too serious and boring. We share different interests in what we consider fun, but I'm willing to conform to her interests as it'll make her feel good.

Danger, Will Robinson.

Lost in Space is so good. Especially the first season

Oct 30, 2020 - 11:04am

Putting aside whether she is the right girl for you or not ... a lot of people equate "fun" with "energy" or "passion." This is true regardless of the activities that you are doing. If you go to dinner and just rehash what happened that day in a monotonous way, that will be perceived as "boring." But if you engage in the conversation like you probably did early in the relationship, tell stories, and act upbeat, this will come across as fun. Put differently, being fun is not activity based but more personality based. Another example ... going to a party doesn't make you fun. Just because you play flip cup doesn't mean you're fun. If you're just going through the motions and don't demonstrate any excitement, you'll still be boring. Note that you should expect her to behave in a similar way when doing your activities - it shouldn't be a one-sided effort.

If you're an introvert, this is definitely going to take effort. I don't think there is really a good trick. As a place to start, consider trying to share certain information in the form of a story rather than just relaying the basic info. It may feel ridiculous and pointless, but it will make you come across as more fun.

Boring Example:

Her: How was work today?

You: It was fine, but my boss dropped a major project on me and asked for it on Monday. I am rather bummed out about the whole thing, but that's the way it goes.

Fun Example:

Her: How was work today?

You: You wouldn't believe it. I was siting at my desk trying to get things finished up before the weekend, when in prances my boss with this big grin on his face. The dude always has that look when he is about to dump something on me. And true to form, he started going off about the importance of the 13-week cash flow... when bam, he told me he needed a draft by Monday morning. So after all that effort, I'm stuck working building a model on Sunday.


The second version, if delivered in an animated way, will generate a lot more excitement from the listener than the first. Not ALL of your interactions need to go this way, but inserting some energy and liveliness into your interactions with your girlfriend (or any women) will go a long way.


  • 11
Oct 30, 2020 - 1:58pm

OP's girlfriend finds spontaneous trips boring so not sure she's going to fall for elaborate storytelling to explain mundane situations.

With that being said, you reminded me of a Chemistry professor I had once who was from the UK. He told us about story telling competitions there where people would be given a simple story and would compete to see who could come up with the longest way of telling the story.

Oct 30, 2020 - 2:20pm

Cheat on her. More sex for you, more drama for her. Win-win for both parties. Who said Demos and Repubs couldn't get along? 

"Full speed ahead, damn the torpedoes." -U.S. Navy General Farragut
  • 3
Oct 30, 2020 - 4:40pm

obviously we need to hear both sides of stories when it comes to relationships, but calling you "not fun" sounds very manipulative... either you are misrepresenting her point of view or you have insecurity issues when around her, in which case you need to speak up about what makes you enjoy your life, and make sure that you two agree to disagree and respect each other, all before going into marriage.

Oct 31, 2020 - 2:11pm

I would advise you read The Five Love Languages, it's a classic book that touches on the emotional needs of each individual in relationships. The way you're describing this search for being a fun guy by "conforming" to her definition of it is a bit of a red flag.

It sounds like she wants to spend quality time with you with activities she finds enjoyable and may even find that as an expression of love on your part (or the opposite of love, indifference). The fact that she keeps saying you're too serious or boring may just be her reaction to having been turned down by her request to hang out at the mall, at a restaurant, etc. I don't think you should force yourself to change your interests, but you should definitely read the book and consider that it's more than just a matter of taking part in activities, but rather creating memories and experiences. 

Oct 31, 2020 - 7:13pm

Don't know if this will help as my pov is coming from a wife/mom, but here goes.

1) take her out to dinner at her favorite restaurants and offer to go shopping with her at the mall. You can carry her bags. While shopping together, exclaim over things that you think are cute, beautiful, funny, unusual, etc. Tell her she looks great in everything that she tries on (within reason).

2) if she's at all open to trying to get into what you love, here's an anecdote from my own life: in the early days of our marriage, my husband was an Eagle Scout and loved camping. I was so...NOT. My husband was smart. He offered to take me camping and do ALL of the work. He literally did 100% of the work. He set up the tent all by himself. He cooked all of our meals on the camp stove/grill. He made the fire and roasted the marshmallows. He did the dishes. I did zilch. I sat in my camp chair, enjoyed all of the delicious food that he cooked, and watched the sunset/read a book. Needless to say, I decided that maybe camping wasn't so bad after all. After a few years of this very imbalanced disparity re: camp chores, eventually when we had kids, I finally jumped in and pulled my share. But until then he treated me like a camp goddess. And it worked. Over the past 3 decades, we've enjoyed many, many years of delightful camping with our family and made many fond memories with our kids splashing in lakes and roasting marshmallows over the campfire. 

So perhaps ask her what exactly it is about the outdoors/camping that she finds so unappealing? For me, it was all of the hard work involved. (I literally grew up never having camped at all and didn't want to have to learn all of those camping/survivalist skills.) Once my husband removed that obstacle, I found it very enjoyable. And, over time, as I gained some camping skills, it became normal for me to join in and help him pitch the tent, cook the side dishes on the camp stove while he started the meat on the grill and made the fire, etc.

  • Analyst 2 in IB-M&A
Nov 1, 2020 - 1:31am

You aren't her entertainment. Tell her to accept you the way you are or get fucking lost. This will solve the problem one of two ways


1) She leaves and problem solved

2) She finds the fact you were dominant to be hot and her shit test is passed.



Nov 2, 2020 - 1:26pm

Equal parts good advice and troll replies in this thread so far. Throwing my $0.01 into the mix hopefully on the good end of the spectrum:

Don't ever fundamentally change who you are for someone else. It's a recipe for unhappiness. Caveat being, if you're some kind of rapist or murderer or animal torturer (etc.), you probably should fucking change. Doesn't seem to be the case for you though.

This is incredibly subjective. Everybody on this board is going to have different advice and maybe none of it will work out for you. Only she knows what she does and doesn't want from you. So, talk to her about it. Communication >, in any relationship, professional or otherwise. If she can't articulate what she means by this, it's a potential red flag to me. Other folks have said you need to be more spontaneous, you need to tease/banter with her (there's a fine line between playful and hurtful here so be careful), that sort of vague stuff. There's no discrete, definitive "one-size-fits-all" answer or example to this type of issue. Have an actual open and honest conversation about this before you take any steps to try and change any part of yourself. 

If she meant that you need to "learn how to have fun her way" ask her what she wants to do. Consider implementing a regular date night (maybe surprise her with the first one). If she only cares about restaurants, stick to food but I'd recommend doing plenty of other stuff too. Examples that have worked for me are hikes, coffee and walks along the waterfront / people watching, days at the beach/lake/river, cooking classes, dance classes, shopping sprees, etc. Not just cookie cutter fancy restaurant crap, although that has its place. If she loves restaurants, maybe start a food tour of your city. My girlfriend and I love trying out random new restaurants, and it's a commonly loved activity among all my friends in relationships, both genders.

Another person suggested reading the 5 love languages - Good call. You don't have to read the entire book but taking one of those generic online quizzes to figure out each others love language can be very helpful. Me and my other half did this, and while we both knew eachother well enough to guess the outcome, it's been helpful to me in my efforts to spoil her and vice versa. 

If your sex life has been, or has recently become, subpar this could be the manifestation of that. Nobody here is qualified to consult you on that, but I'd say being more spontaneous and trying new positions helps. Maybe jump her in the kitchen when she gets home. Or maybe she only wants missionary in the dark, on Saturdays. Again, communication with her on this topic is key.

You've said you enjoy each others company and have a lot in common - How long have you been together? What's your typical week look like? Typical date night? In my opinion, women ultimately fall for the "fun" guys, so has anything changed since you two first started dating? Is this "you're no fun" stuff a new thing? Everybody goes through troughs and peaks. Nobody is consistently in the same mood throughout their entire life - maybe you're in a rough patch and its affecting your relationship? I tend to shut down on my girlfriend whenever I'm on a work-bender but we've found ways to address that.

Finally, you may have "fun" hobbies and passions (U-haul camping sounds awesome as others have said), but you may not be "fun" to talk to. If all you ever talk about is work/school/finance/etc., she's gonna find you boring. I struggle with this sometimes with my girlfriend and even with the boys (most of whom are non-finance). I start talking about some cool deal or some intricate model or something and everybody's eyes invariably glaze over and I start getting chirped for being a nerd. Know your audience.

I hope you two figure it out. 

Nov 7, 2020 - 10:08pm
Start Discussion

Popular Content See all

What would you name your MM Bank?
+30OFFby 1st Year Analyst in Investment Banking - Mergers and Acquisitions">Analyst 1 in IB-M&A
What are your thoughts on living in SF?
+23IBby Prospective Monkey in Investment Banking - Mergers and Acquisitions">Prospect in IB-M&A
I farted and my coworker smelled it
+19OFFby 1st Year Analyst in Investment Banking - Industry/Coverage">Analyst 1 in IB - Ind

Total Avg Compensation

November 2020 Investment Banking

  • Director/MD (18) $713
  • Vice President (52) $334
  • Associates (272) $228
  • 3rd+ Year Analyst (39) $161
  • 2nd Year Analyst (153) $153
  • Intern/Summer Associate (139) $139
  • 1st Year Analyst (593) $130
  • Intern/Summer Analyst (566) $82

Leaderboard See all

LonLonMilk's picture
Jamoldo's picture
Secyh62's picture
redever's picture
CompBanker's picture
bolo up's picture
bolo up
Addinator's picture
frgna's picture
Edifice's picture
NuckFuts's picture