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Dating-Age |OT4| Realise You're Living in the Golden Years

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I echo what others here have said. It seems like your time with that girl was an emotional roller-coaster. The main reason why I would end it is that it seems to have gotten way too complicated for a relationship. Reading the timeline of events literally made it seem like you guys went through some kind of maze while together.
Yeah you could say that :lol I agree that it seems way too complicated, perhaps she sees it the same way. The main reason for her not being interested in a relationship with me was because she felt like she wasn't good enough. I never felt that way, more of the opposite if anything, but she sometimes took things as she was doing things wrong, based on my reactions, and it got old real quick. But hopefully I've explained myself and how wrong she is in believing that. Letting go of her past was the biggest hurdle for me and I genuinely think we could work it out if we do it together, which is key. So the rest is up to her, it's not like I can keep on sending flowers and write sonnets forever. This is supposed to be give and take and it's mostly giving on my part and taking on hers at the moment. And that has got to stop one way or another, for sure. Two of you guys have mentioned mazes now, maybe there's something to that. As it stands, it would definitely seem like I'm losing the fight, but that's okay too, I believe that's better than not even trying. I won't regret this, not like I would've regretted doing nothing about the situation.

She mentioned she lives down the road from work, I asked her if she lives with her boyfriend, she confirmed she doesn't have one. Simple, but effective. And I am, but I think it's more of a casual dinner rather than a date, as I was (jokingly) poking fun at her cooking and she wants to prove me wrong. How do I take it from a friendly 'challenge accepted' scenario to a date?
Like Idde said, mission accomplished. Usually I'd assume it's a date in that situation but since she's a work mate, caution may be advised. Go in just expecting a good time and see if she likes and reciprocates your touch etc.

With all said, are there any regulars who'd like to keep in touch over facebook?
 
Like Idde said, mission accomplished. Usually I'd assume it's a date in that situation but since she's a work mate, caution may be advised. Go in just expecting a good time and see if she likes and reciprocates your touch etc.
That's kinda the one thing thats making me a bit 'eh' about this - what if I go in giving off a 'date' vibe when it really is nothing more than a friendly dinner? It could make work very awkward.
 
That's kinda the one thing thats making me a bit 'eh' about this - what if I go in giving off a 'date' vibe when it really is nothing more than a friendly dinner? It could make work very awkward.

You need to go in casual and get a feel for how she's taking it. If you jump the gun and try to be all "datey" and she thinks it's a friend thing it will be weird. Go in with the friend mentality and give off casual signs that you're interested in more. Flirt with her - see if she flirts back. Casually touch her arm or hand - see if she reciprocates. After a full dinner with her you should be able to get the vibe if she's into you or not. Then ask her out again at the end of the date, see what happens. You're gonna need to put yourself out there at some point and take a chance, and it could blow up in your face. But as long as you don't storm off in a huff if she says she just wants to be friends, you should have no problem at work the next day. And if she IS into you then you're gonna walk away from the date brimming with confidence.
 
You need to go in casual and get a feel for how she's taking it. If you jump the gun and try to be all "datey" and she thinks it's a friend thing it will be weird. Go in with the friend mentality and give off casual signs that you're interested in more. Flirt with her - see if she flirts back. Casually touch her arm or hand - see if she reciprocates. After a full dinner with her you should be able to get the vibe if she's into you or not. Then ask her out again at the end of the date, see what happens. You're gonna need to put yourself out there at some point and take a chance, and it could blow up in your face. But as long as you don't storm off in a huff if she says she just wants to be friends, you should have no problem at work the next day. And if she IS into you then you're gonna walk away from the date brimming with confidence.
That's some good advice right there, cheers.

Also, unrelated, just got a date on OKCupid. Literally started talking to this girl an hour or so ago, hit it off and we're going on a date next week. Only thing thats putting me off? She's an escort. Deal or no deal, GAF?
 
That's some good advice right there, cheers.

Also, unrelated, just got a date on OKCupid. Literally started talking to this girl an hour or so ago, hit it off and we're going on a date next week. Only thing thats putting me off? She's an escort. Deal or no deal, GAF?

Tell her you'll be escorting her.
 
Tell her you'll be escorting her.
The topic of sex has already been bought up, naturally. She seems up for a 'rough fuck' without me paying. Her words, not mine. It would still feel like I'm actually paying for her services, mind, although she's said I won't. I'm dubious - but she is pretty damn cute.
 
So guys, theres this girl how rejected me two years ago over another guy, and now that she dumped his boyfriend she wants me

But i dont want to be like the easy second option for her, its just ego or should i accept her?
 
So guys, theres this girl how rejected me two years ago over another guy, and now that she dumped his boyfriend she wants me

But i dont want to be like the easy second option for her, its just ego or should i accept her?

Do you like being the also ran, the runner up, the second option? If so, then yes, go after her tiger.
 
So guys, theres this girl how rejected me two years ago over another guy, and now that she dumped his boyfriend she wants me

But i dont want to be like the easy second option for her, its just ego or should i accept her?

How long has it been since she dumped him?
 
So guys, theres this girl how rejected me two years ago over another guy, and now that she dumped his boyfriend she wants me

But i dont want to be like the easy second option for her, its just ego or should i accept her?

You still have feelings for this girl after two years?
 
So guys, theres this girl how rejected me two years ago over another guy, and now that she dumped his boyfriend she wants me

But i dont want to be like the easy second option for her, its just ego or should i accept her?

Good God man, have some self-respect for yourself. Tell her to fuck right off.


Or hate-fuck her and never talk to her again.
 
Do you like being the also ran, the runner up, the second option? If so, then yes, go after her tiger.

Fuck NO!

How long has it been since she dumped him?

Two days and alredy contacted me... to talk
You still have feelings for this girl after two years?
Sure but not strong feelings like the need to be with her

Good God man, have some self-respect for yourself. Tell her to fuck right off.


Or hate-fuck her and never talk to her again.

Your second option seems fucked-up but ill think about it
 
Yeah I kinda hate myself for still loving her, for not listening to her better and for having been so damn egotistical so she's been hurt. Creating a healthy relationship after all this is probably impossible, yeah. There's always the possibility that I'm just attached simply because she's the first adult girl to show so much affection for me. I barely know what a healthy relationship looks like, at least not from personal experience. I appreciate the hard questions, but I can't really answer them which might be telling :) I agree that love shouldn't feel like this or be this complicated though. I recognize that there are a million things that make this thing sound terrible and doomed, and it probably is, I'm not gonna deny that. Like I said, I have left her twice and like she has pointed out several times, she has not ever felt a need to that and she's been really hurt over that fact, it's been simmering down below between ever since. But as many negative points as there may be, we both agree that we've been a good fit when things have been great, it has been worth it for her too and we both have acknowledged that we have plenty of positive memories to cherish, her words. The difference is that I want to make more memories with her specifically and that's what I've been trying to convince her of helping me with. She showed me that life can be sweet and I have never felt more comfortable around a woman before and she provides an intriguing challenge that makes me want to propel forward and grow. I've enjoyed the emotional (shit)storms we've had, I do believe I've learned a lot from them and I appreciate her part in my life all the more because of everything we've done together. Even in our hardships, she has shown me what a lovely girl she truly is and my affection for her has never really wavered even in our darkest moments. But yes, I am deeply attached and she's not, and it's hurting me like hell. Perhaps there is too much shit going on to make this work. I honestly can't tell when this attachment happened or what she did.
you're projecting all kinds of stuff on to this girl. I don't think its fair to her and its going to leave you heartbroken in the end. Youre in love with the idea of being in love, take the blinders off.

I don't have much else to say. It will implode again, you'll feel like shit and the cycle will continue. Just know your future suffering and heartache in this situation will be self inflicted. You'll have no one else to blame but yourself
 
The topic of sex has already been bought up, naturally. She seems up for a 'rough fuck' without me paying. Her words, not mine. It would still feel like I'm actually paying for her services, mind, although she's said I won't. I'm dubious - but she is pretty damn cute.

Watch out for this girl. Saying to customers that they don't need to pay is a pretty well known trick: she will ask for money during the date, or she will ask you anyway once she is done (and get the money either by guilt trip or through insults) or, even worst, she may unleash her "driver" on you.
So: if she comes in a car she is not driving, RUN.
 
She wants the D

Smang it man.

Smash it and bang.
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you're projecting all kinds of stuff on to this girl. I don't think its fair to her and its going to leave you heartbroken in the end. Youre in love with the idea of being in love, take the blinders off.

I don't have much else to say. It will implode again, you'll feel like shit and the cycle will continue. Just know your future suffering and heartache in this situation will be self inflicted. You'll have no one else to blame but yourself
I probably am, the thoguht has occurred to me as well, so you're probably right as always :) In most likelyhood I'm just holding on for dear life due to scarcity and she's the only girl who gives me the attention I crave (from someone attractive at least). She's not the last girl alive and I have several girls who show interest. I've been working under the impression for quite a while that it's over for good but not subconsciously as well. It's time.
 
So I've been talking to my female friends about how I've been fucking things up lately and they say that the problem is that I have sex too early. I couldn't get a clear answer for when they think it is a good time.

Granted the sex was early, but its not like it was forced or awkward. It just happens. The problem seems to arise a few days when they lose interest despite things going so well before that. And no GAF I do not have a small penis nor am I terrible in bed.

My friends say that this is because this makes them think I was only interested in hooking up.

I don't agree since I still show the same interest after as I did before.

I have no idea. I'm getting frustrated repeatedly having to start anew after that point.

What do you guys think about the topic?
 
http://www.thezooom.com/2013/01/10596/

Sex too early sounds odd. It's not like you forced it on them so they clewrly wanted it too. And casual hookups are not a bad thing either, that's just something we've been taught we shouldn't want or do, more so if you're a girl. And it's bullshit. Maybe your friends are right and your girls thought that's all you wanted for whatever reason but it's still silly and might just boil down to bad luck. I wouldn't worry about it.
 
How much does living with my parents hurt my chances of dating? I'm 23 with a stable job, no debt, and could rent an apartment at any time (and nearly did). I'm saving for a house though, and with current prices it'll be about 3 more years before I can even start looking. Paying rent would only make the wait even longer.

I'm lucky enough that my parents live close to my job, and even more that they let me stay for free. Should I just hold off on dating until I can secure my own place?
 
How much does living with my parents hurt my chances of dating? I'm 23 with a stable job, no debt, and could rent an apartment at any time (and nearly did). I'm saving for a house though, and with current prices it'll be about 3 more years before I can even start looking. Paying rent would only make the wait even longer.

I'm lucky enough that my parents live close to my job, and even more that they let me stay for free. Should I just hold off on dating until I can secure my own place?

It is only an issue if you make it an issue.
 
So I've been talking to my female friends about how I've been fucking things up lately and they say that the problem is that I have sex too early. I couldn't get a clear answer for when they think it is a good time.

Granted the sex was early, but its not like it was forced or awkward. It just happens. The problem seems to arise a few days when they lose interest despite things going so well before that. And no GAF I do not have a small penis nor am I terrible in bed.

My friends say that this is because this makes them think I was only interested in hooking up.

I don't agree since I still show the same interest after as I did before.

I have no idea. I'm getting frustrated repeatedly having to start anew after that point.

What do you guys think about the topic?
If you show the same interest as before, maybe they're the ones who were only interested in a hook up. Honestly, if someone likes you, they're not going to write you off because you had sex "too early."

How much does living with my parents hurt my chances of dating? I'm 23 with a stable job, no debt, and could rent an apartment at any time (and nearly did). I'm saving for a house though, and with current prices it'll be about 3 more years before I can even start looking. Paying rent would only make the wait even longer.

I'm lucky enough that my parents live close to my job, and even more that they let me stay for free. Should I just hold off on dating until I can secure my own place?
I'm sure there will be some people who'll have an issue with it but honestly it's not that big of a deal. Just gotta be extra quiet. :x
 
I probably am, the thoguht has occurred to me as well, so you're probably right as always :) In most likelyhood I'm just holding on for dear life due to scarcity and she's the only girl who gives me the attention I crave (from someone attractive at least). She's not the last girl alive and I have several girls who show interest. I've been working under the impression for quite a while that it's over for good but not subconsciously as well. It's time.
as long as you understand what you're getting into. Best of luck
How much does living with my parents hurt my chances of dating? I'm 23 with a stable job, no debt, and could rent an apartment at any time (and nearly did). I'm saving for a house though, and with current prices it'll be about 3 more years before I can even start looking. Paying rent would only make the wait even longer.

I'm lucky enough that my parents live close to my job, and even more that they let me stay for free. Should I just hold off on dating until I can secure my own place?
if you're fun, sociable and aren't ashamed of it, you'll be fine. If someone has a big issue with it, that's their problem and not yours. It's never too early to start seeking connection

Also, dating isn't like applying for a fucking bank loan or something "I have no debt and a steady income" please never let this leave your mouth on a first date, unless stated ironically
 
Also, dating isn't like applying for a fucking bank loan or something "I have no debt and a steady income" please never let this leave your mouth on a first date, unless stated ironically

Hope so! I'm flying blind here with regards to relationships; none in my friends or family have functional ones, so I really don't have any examples to work from. For my parents, dating/marriage was a business, and they drilled that stuff in. This thread's definitely helped me see what a "normal" relationship looks like, thanks!
 
How much does living with my parents hurt my chances of dating? I'm 23 with a stable job, no debt, and could rent an apartment at any time (and nearly did). I'm saving for a house though, and with current prices it'll be about 3 more years before I can even start looking. Paying rent would only make the wait even longer.

I'm lucky enough that my parents live close to my job, and even more that they let me stay for free. Should I just hold off on dating until I can secure my own place?

1st Things; Simply living on your own isn't going to magically make you start slaying pussy by itself. Has living at home hurt your chances so far? How many dates have you been on recently? How many GFs have you had? Where do you live (USA)?

There's no reason to hold off dating until some hypothetical future date when you're living on your own. Start living life RIGHT NOW. Otherwise, you'll always find a reason to hold off dating.

The answer you seek depends almost entirely on the lady you meet. Seriously. You're still fairly young at 23yo. So there's a good chance any lady that you meet around your age is, or was recently in the same position of living at home. If you meet a lady and have a connection with her, then it's doubtful she'd write you off simply because you live with your parents.

But make no mistake, living at home at 23yo sure isn't helping your chances either, especially if you plan on doing so for another 3yrs. And I wouldn't count on landing a professional lady (with an education, career, her own place, etc) until you're on your own.
 
as long as you understand what you're getting into. Best of luck
I think I do, only time will tell if this will work out or not. I'm done crying over spilled milk either way though :) Thank you. Facebook?

How much does living with my parents hurt my chances of dating? I'm 23 with a stable job, no debt, and could rent an apartment at any time (and nearly did). I'm saving for a house though, and with current prices it'll be about 3 more years before I can even start looking. Paying rent would only make the wait even longer.

I'm lucky enough that my parents live close to my job, and even more that they let me stay for free. Should I just hold off on dating until I can secure my own place?
Living at home might be odd but as always, if a girl doesn't want to date you because of that, or anything else, she's not one you'd want to spend time with anyway, right? I do have to question why you'd want to buy a house at such a young age though (also, bank loans? Couldn't you get a house tomorrow that way?). A house is WAY more responsibility than one thinks, not only because of its size compared to an apartment but it also ties you down tremendously.
 
Hope so! I'm flying blind here with regards to relationships; none in my friends or family have functional ones, so I really don't have any examples to work from. For my parents, dating/marriage was a business, and they drilled that stuff in. This thread's definitely helped me see what a "normal" relationship looks like, thanks!
It's good you realize that solely treating people like a commodity isn't a winning strategy. Like you said, it hasn't worked for those in your life so far
Facebook?
do I have facebook? No. I got rid of it last summer after my gf moved away. I realized the only reason I used it was to virtually stalk her... It wasnt health and wasnt helping me move on. Truth be told, I don't miss it
 
If you show the same interest as before, maybe they're the ones who were only interested in a hook up. Honestly, if someone likes you, they're not going to write you off because you had sex "too early."

Not so much they write me off. I think it literally changes things. Feelings, pacing, tension. I'm only 20 and a lot of girls i know put sex on a pedestal. I guess it is an "immaturity" thing.
 
I'm not sure it matters when one have sex? I mean, the last one I were with for 15 months I had sex with on our first date. That was the same case my ex who came before her.

Of course my way of dating is totally untraditional, as I have never done the "1st date, 2nd date, 3rd date etc." in my past 7 relationships but I can't say any of them have been total successes haha.

Though, I plan on going slow with my next date and I also want my next one to be local. It's gonna be exciting and interesting.
 
Some thoughts on this.

Last weekend a friend mentioned I'm too wild. I'm not going to be able to be in a relationship for about a year or two. Basically I have too much energy and unsure about what I want myself. Was talking to another friend who mentioned that I'm the type of person who needs to travel. Saying along the same lines, where I need to get away from where I am to find myself. Both saying I need to naturally calm myself down and find what I want.

This is normal right?
 
So this girl on Zoosk sent me a message several days ago and has checked out my profile quite a few times since then. Unfortunately, messaging members is behind a fucking paywall and I'll be damned if I'm going to pay only to see that it was a fuckin spam bot or something. Has anyone here had any experience paying for Zoosk?
 
Just a comment about a poster asking about having his own place, plus other things. There will always be women who have certain financial demands for any relationship they enter. What would I personally do? Nothing.

One thing I have learned is that you always want to do things for yourself first. So, say some beautiful woman wants you but demands you own a car. Don't start scrambling and selling your kidney for a car. It is true that there will be women who refuse you because you may lack certain assets. However, there will also be women who appreciate you and want you regardless.

Do things at your own pace, ignore pressure. So, how do you approach women even though you have no car, apartment, or whatever? Well, just approach them! Part of the lure is you want to make them comfortable with you regardless of whatever "deficiencies" you may have.

One of my friends has been banging girls left and right. He has no car, apartment - heck, he doesn't even have a license to drive! At the end of the day you have to accept and be comfortable with what you have.

This is the advice I'd give to either a man or woman asking.
 
Hey guys. I need some advice. Every time I make any progress with girls, I get my hopes up and get way too excited. A girl just canceled on our date a bit ago, and now I'm just sitting here, listening to music and feeling bummed out. She seems like she still wants to hang out at some point, but I've been looking forward to it for what seems like a long time. This isn't a one-time thing, it happens with the admittedly few girls I do meet - it's a pattern. It's always too good to be true.

My point is, it seems like a no-win situation. If I get excited and get my hopes up, I have the chance of being let down. But if I let myself not care, then it's just that - I don't care, so I won't make any effort to schedule any dates or try to look nice or even enjoy myself with the girl.

How do I balance caring too much vs. caring too little?

P.S I have far too little experience for my age, so that may have something to do with it.
 
Hey guys. I need some advice. Every time I make any progress with girls, I get my hopes up and get way too excited. A girl just canceled on our date a bit ago, and now I'm just sitting here, listening to music and feeling bummed out. She seems like she still wants to hang out at some point, but I've been looking forward to it for what seems like a long time. This isn't a one-time thing, it happens with the admittedly few girls I do meet - it's a pattern. It's always too good to be true.

My point is, it seems like a no-win situation. If I get excited and get my hopes up, I have the chance of being let down. But if I let myself not care, then it's just that - I don't care, so I won't make any effort to schedule any dates or try to look nice or even enjoy myself with the girl.

How do I balance caring too much vs. caring too little?

P.S I have far too little experience for my age, so that may have something to do with it.

My only tip would be seem like you are busy with a lot of stuff, if said girl told you a week later she wanted to do something, don't respond within 5 minutes. Let her wait, or even let her get denied

Although, if someone did that to me i wouldn't bother with them in the future.

note: i'm not really an expert, just my personal input.
 
My only tip would be seem like you are busy with a lot of stuff, if said girl told you a week later she wanted to do something, don't respond within 5 minutes. Let her wait, or even let her get denied

Although, if someone did that to me i wouldn't bother with them in the future.

note: i'm not really an expert, just my personal input.

But see, that may change what I look like to her, but it doesn't actually change my mental state. Even if I'm waiting an hour or two to text her back, I'm still thinking about it for those two hours.
 
But see, that may change what I look like to her, but it doesn't actually change my mental state. Even if I'm waiting an hour or two to text her back, I'm still thinking about it for those two hours.

I'm a very negative person, I always expect the worst possible scenario, so whenever a girl accepts to go on a date with me I always expect(assume) them to cancel at some point. To this day, every girl that has accepted my date invitation has cancelled on me. I was never bummed out afterwards because I expected them to cancel on me so I never got my hopes up.

It has worked for me, so perhaps you should try something similar?
 
I'm a very negative person, I always expect the worst possible scenario, so whenever a girl accepts to go on a date with me I always expect(assume) them to cancel at some point. To this day, every girl that has accepted my date invitation has cancelled on me. I was never bummed out afterwards because I expected them to cancel on me so I never got my hopes up.

It has worked for me, so perhaps you should try something similar?

Yeah, I'm pessimistic like that too. But if I had that mindset with girls, I wouldn't even try. I wouldn't even ask them out if I "knew" that they were going to cancel.
 
Guys, no. You're not supposed to be pessimistic, even if that's very tempting (trust me, I know). What you're supposed to be is neutral. You're not supposed to care! Because while the girl is busy cancelling you're busy getting another number.

The mindset you should adopt is the following: get the number, set a date. Keep contact minimal until then. Does she cancel? Who cares, continue going about your day. If you like her then go on a date if SHE offers to reschedule. Otherwise? Move on and forget about her.

I swear, life is so simple this way. I can proudly say I never have girl problems. I might have academic problems, a bit of a slump in basketball, but no girl issues. Ever. Trust me on this one.
 
Hey guys. I need some advice. Every time I make any progress with girls, I get my hopes up and get way too excited. A girl just canceled on our date a bit ago, and now I'm just sitting here, listening to music and feeling bummed out. She seems like she still wants to hang out at some point, but I've been looking forward to it for what seems like a long time. This isn't a one-time thing, it happens with the admittedly few girls I do meet - it's a pattern. It's always too good to be true.

My point is, it seems like a no-win situation. If I get excited and get my hopes up, I have the chance of being let down. But if I let myself not care, then it's just that - I don't care, so I won't make any effort to schedule any dates or try to look nice or even enjoy myself with the girl.

How do I balance caring too much vs. caring too little?

P.S I have far too little experience for my age, so that may have something to do with it.

I remember telling my therapist about the "not letting yourself get excited" rule and he made a good point that it's ok to be excited, it's normal, but you should learn how to temper your excitement/expectations with a bit of healthy indifference.

Be excited, but don't build it up to insane levels. Also have a backup plan if she bails on date night, do not sit at home and ruminate in a "forever alone" pity party. Make sure you have other things in your life past the possibly of dating a girl that you are excited about, that way you don't put all your eggs in one basket.

Sometimes taking a deep breath and writing down things in a logical way helps keep things in perspective, i.e. "Girl just got out of a relationship, so she might not be ready to date yet".
 
Guys, no. You're not supposed to be pessimistic, even if that's very tempting (trust me, I know). What you're supposed to be is neutral. You're not supposed to care! Because while the girl is busy cancelling you're busy getting another number.

The mindset you should adopt is the following: get the number, set a date. Keep contact minimal until then. Does she cancel? Who cares, continue going about your day. If you like her then go on a date if SHE offers to reschedule. Otherwise? Move on and forget about her.

I swear, life is so simple this way. I can proudly say I never have girl problems. I might have academic problems, a bit of a slump in basketball, but no girl issues. Ever. Trust me on this one.

The process you describe is what I do, it's the stress and nervousness that I don't like. I'll be honest with you, I was mostly relieved that she cancelled, because if we had gone on the date, I would have had to kiss her since it's the 3rd date, and I get crazy nervous about that stuff. I know it's weird that I want to kiss her and don't want to kiss her at the same time, but whatever.

And it's easy to say all that when you're getting numbers all the time, but what if you're not? I'm terrible with women, I've only been on 3 dates this year, with my 1st one ever near the beginning of the year. How can I not stress about it when I'm in my 20's and have virtually no experience? If things don't go well then it's another unknown amount of time trying to find another girl.

Make sure you have other things in your life past the possibly of dating a girl that you are excited about, that way you don't put all your eggs in one basket.

But that is about the most exciting thing that can happen to me right now. I've got a good job that I like, went to a great college for a great education, I've got my own place, saving up for a car, etc. If I do say so myself, I excel in most areas in my life, except for this one, which for some reason is a massive gaping hole. It only makes sense to focus on this part.
 
Hey guys. I need some advice. Every time I make any progress with girls, I get my hopes up and get way too excited. A girl just canceled on our date a bit ago, and now I'm just sitting here, listening to music and feeling bummed out. She seems like she still wants to hang out at some point, but I've been looking forward to it for what seems like a long time. This isn't a one-time thing, it happens with the admittedly few girls I do meet - it's a pattern. It's always too good to be true.

My point is, it seems like a no-win situation. If I get excited and get my hopes up, I have the chance of being let down. But if I let myself not care, then it's just that - I don't care, so I won't make any effort to schedule any dates or try to look nice or even enjoy myself with the girl.

How do I balance caring too much vs. caring too little?

P.S I have far too little experience for my age, so that may have something to do with it.
I love the hell out of this question, here's why. You're questioning your actions, motives, feelings and examining the emotional cause and effect therein. That's great! I believe questioning things and always asking "why" is an important step to stay on track during the self improvement process...but I digress.

Being excited to meet new women is natural, it shouldn't be supressed so much as maintained to avoid growing out of control. Like youve already stated, it's about balance. You need to be realistic and grounded. This goes back to something I've harped on a lot in the past....where do you get your value? If youre getting overly disappointed with someone you barely know canceling a date, it begs the question of where that disappointment comes from. Is just the act of spending time with a girl boosting your self worth? Do you need that female attention to feel good about yourself? Does that sound healthy? (
pro-tip: it isn't
) Would your life really be that much better if you had hung out? Would you consider perhaps you over hyped this shit and blew it out of proportion to begin with. These are questions worth asking so you can change how you're approaching this whole dating thing and avoid the pitfalls next time around.

I think it's partially about controlling yourself when it comes to expectations. You can't go all overly attached girlfriend before a date. You can't allow yourself the pleasure of running away with your imagination, no matter how tempting. Depending upon how much dating you do, how lonely you are and how experienced you are with women, this can be a very difficult task. A guy who is going on his first date in 3 years will want to hit it out of the park, one and done. However in the game of dating, that's rarely the case. Reality and unrealistic expectations meet, it leads to disappointment. And the higher you go, the greater the fall. Sometimes we fall really hard, I know I have.

Becoming too excited too soon gives off needy vibes as well. If you're eager to bendover backwards to hangout, it suddenly looks like you dont have much of a life or obligations to worry about. Dropping everything to spend time with someone you barely know screams desperate.

These issues can be better handled with experience. they can be tackled even faster if you're dating a lot and have a large number of women in your life. Those aside, my big piece of advice is to stay grounded. Going to meet a new girl for coffee? Keep pounding it into your head that it's just. fucking. coffee. You're not vetting a future wife, you're not looking to impress someone you dont even know. It's to talk. You're there to enjoy their company and get to know someone. if anything she needs to impress you because you're an awesome motherfucker that doesn't have time for games or immaturity. When you keep it light and fun, it makes the entire process of meeting new people a million times easier. Less expectations, less stress. They end up canceling? No biggie, because at this point, you've held the expectation that it was just fucking coffee.

Apologizes if this was super disjointed, posting from my iPod.

Edit: I started typing my post out a while ago so I missed some stuff. But this
I remember telling my therapist about the "not letting yourself get excited" rule and he made a good point that it's ok to be excited, it's normal, but you should learn how to temper your excitement/expectations with a bit of healthy indifference.

Be excited, but don't build it up to insane levels. Also have a backup plan if she bails on date night, do not sit at home and ruminate in a "forever alone" pity party. Make sure you have other things in your life past the possibly of dating a girl that you are excited about, that way you don't put all your eggs in one basket.

Sometimes taking a deep breath and writing down things in a logical way helps keep things in perspective, i.e. "Girl just got out of a relationship, so she might not be ready to date yet".
is good stuff. Stn knows what's up too
 
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