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

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Is there some golden rule regarding asking people out that work at stores?

Always wondered this. It seems like given their job, they are kind of forced to talk to you and it makes the whole thing feel really weird and unfair for them. Not to mention the fact that a lot of the time, the charm or pleasant attitude they have is most likely not genuine.

That's what dawned on me today after I set up my UPS mailbox. I spent a whole bunch of time analyzing whether she was into me or not, from her laughing and light flirting. Then I realized she's a cashier, she's supposed to be all nice and shit. Really made me feel stupid.
 
She seems a little vain and hyper, like the kind of person who would be really nice to talk to for a few moments but would drive you insane if you were stuck sitting next to them on a long flight or something. That's way too much information. Since the guy will know everything about her prior to the first date, she's going to be questioning him the whole time, and it's up to him to keep the conversation going.

Just to play devil's advocate though, at least she knows herself. That's doing better than I was at that age.
 
I've seen it work but mostly with waiters. (Writing your number on the receipt.) That kind of takes away the unfairness for the situation since they don't have to directly deal with you if they don't want to.

I don't think it's something I could personally do but I've also been asked out by people working the cash register which kind of has a lot of the same weirdness. If they're polite and cool about it though, it's not as weird or unpleasant as it could be.

It's one of those things where it really depends on the person and I can see some people not caring about it and others being really frustrated with it. So basically, my point is, there doesn't seem to be a golden rule, no. :P
That's what dawned on me today after I set up my UPS mailbox. I spent a whole bunch of time analyzing whether she was into me or not, from her laughing and light flirting. Then I realized she's a cashier, she's supposed to be all nice and shit. Really made me feel stupid.

Thanks guys.

I guess I have something to think about.
 
No, I don't think you're being cynical or jaded. But from you told me about her last relationship I can tell you that going through a divorce can absolutely change what you expect out of your relationships. It's different for everyone obviously but I can understand why she wants to feel "swept off her feet". Personally, I can tell you that I am much less patient with relationships and a bit quicker to decide whether or not to continue seeing someone. Maybe I've given up on relationships too soon, maybe not. I don't expect to be 'swept off my feet' because I don't know if I believe in it or if i'd trust a feeling like that.

Another thing to consider is that she might be scared and afraid of getting hurt. Gun shy and not even realize it.

I'm somewhat surprised to hear her say she still wants to do whatever it is in a couple of weeks. Regardless of what she wants I'd be careful getting together with her. You obviously still care about her but it might make it harder to let go.
I can definitely appreciate the notion that a divorce after a long marriage is likely to change a person's perspective. I feel like I give her plenty of latitude in that regard. I haven't had that experience, so I acknowledge that I can't see the other side of it very well. I have tried to express the idea that she might just be distrustful of the first serious relationship on the other side of that. It's just really hard to do that without sounding patronizing. Whatever the reason, I accept that I just can't truly know her motivations.

And I must say, I'm feeling a lot more at ease with the situation than I was even just a couple of days ago. I'm still not completely convinced that it's totally over, but I'll be okay if it is

I think I am inclined to see her again, even if in a platonic context. I know it'll be hard, but I really enjoy her company. I spent two years at school seeing her three days a week and knowing I couldn't have her despite being crazy about her. So I've got plenty of experience resigning myself to that fact.

Whatever the case, I'm in no rush. We'll see how it feels in a week or two.
 
Gaf, what do you do when you go out by yourself at night?

I just wasted another saturday night on the internet and I'm feeling a little guilty about it. But then again, I have tried going out by myself on other occasions, but I just can't get social, and each time I end up being a creepy loner who just stands and drinks. The drinking doesn't help, as I remain 100% self-conscious anyway.

I have no one to go with me, since I don't know anyone in this city yet. And my coworkers don't count.
 
Gaf, what do you do when you go out by yourself at night?

I just wasted another saturday night on the internet and I'm feeling a little guilty about it. But then again, I have tried going out by myself on other occasions, but I just can't get social, and each time I end up being a creepy loner who just stands and drinks.

I have no one to go with me, since I don't know anyone in this city yet. And my coworkers don't count.
As far as clubs and bars go, I've never been to one alone and I'd probably be the person being awkward sitting alone too. :P But if I have no one to hang out with and want to go do something, using websites like meetup.com and finding a group of people doing something interesting works well. :) There are meet ups like Drink & Draw that can be really fun and they'll be plenty of people going alone to stuff like that.
 
As far as clubs and bars go, I've never been to one alone and I'd probably be the person being awkward sitting alone too. :P But if I have no one to hang out with and want to go do something, using websites like meetup.com and finding a group of people doing something interesting works well. :) There are meet ups like Drink & Draw that can be really fun and they'll be plenty of people going alone to stuff like that.

Well, I don't think people in my country use any websites like that.

When I'm go alone, it's usually somewhere that's playing music I like, so the night is never entirely wasted. I've been to some pretty good rock/metal covers like that. Today I was thinking about doing something different, but a cold and thinking about all the past failures killed the mood.

And now I'm sad that I will have to wait a whole week for the next chance =(
 
So I posted in this thread a little over two and a half months ago about doing long distance. Not too long after that my (now EX) girlfriend broke up with me, which was hard as we had been best friends for four years prior to our relationship. It was by no means an easy thing to go through, but being away from home and at a University in a different province definitely helped the process. She wants to get back together after University and get married, but in the mean time we need to be best friends still, and etc. I realize the complete idiocy in this plan and don't plan to be her punching bag in this matter. Since then, I've been trying to move on and I feel I have been doing a fairly good job at it. I met a girl in my film class that seems to be everything I could ever want in a partner, but after being in a relationship for so long I have no idea what to do. Don't want to ruin things, as just being around her reminds me of happier times with a happier me.
 
Gaf, what do you do when you go out by yourself at night?

I just wasted another saturday night on the internet and I'm feeling a little guilty about it. But then again, I have tried going out by myself on other occasions, but I just can't get social, and each time I end up being a creepy loner who just stands and drinks. The drinking doesn't help, as I remain 100% self-conscious anyway.

I have no one to go with me, since I don't know anyone in this city yet. And my coworkers don't count.
My friend goes out to bars by himself all the time and actually loves it. He says the key is to bounce around between bars. Never stay somewhere for a prolonged period of time. It's when you stand around for hours by yourself that you start to look like a creep.
 
Well, I knew things were too good to be true with the Jewish girl. For the record, I already knew the score...Her dad's pretty controlling and doesn't want her to be in a relationship with a non-Jew and she's even sort of got it ingrained that she has to continue the Jewish line etc, even though her younger sister and older brother don't give two shits about it. She feels singled out or that her dad will come down heavy on her (well, he's basically said as much) if she starts seeing a non-Jew seriously.

Our dates have been fantastic - we've both really enjoyed each other's company, she totally digs me, I totally dig her, she's cool and intelligent, she thinks I'm hilarious, and she loves my eyes and smile. On our first two dates drink was always involved and we'd started making out towards the end of the evening like it was our first time or something. It was exciting. She even said after our second date that we couldn't keep doing this and she didn't know if she truly liked me because she wasn't completely sober. So I just gave a non-caring answer like "If you think it's best we don't continue seeing each other, I totally understand".

So a week or so later we have a 3 hour Skype call. I ask her out for dinner on Saturday and she agrees. Then she starts trying to justify herself by going on about how she finds me really fun to be around and she that she won't drink this time.

So Saturday comes around (last night), we go to dinner, have a right old laugh in the restaurant. She always stares at me uncontrollable, so I reciprocate. She says she finds my stare quite powerful. She also can't hold her shit together when I start staring and smiling at her, which I find cute.

A few minutes before we left the restaurant, she started going all coy. I tried to get her to spill the beans, but she wasn't biting. When we did leave the restaurant, she got right in my face, looked at me innocently, and started moving her face closer to mine. So we started kissing again - but this time we're completely sober (ok, I had 1 glass of wine, but she had been drinking water the whole time). Then I said "We should probably go somewhere better than standing in front of the restaurant entrance". She started giggling uncontrollable again and we went round the corner into Hyde Park.

She eventually told me why she went all coy before, and it was because she felt butterflies for the first time [with me] as I stared into her eyes in the restaurant. We found some deck chairs (lol) and just sat down talking about stuff for ages, getting cosy, laughing like children at the funny noises the ducks were making, and kissing.

Now, I wouldn't have done this if she didn't mention the 'butterflies' things and in hindsight maybe 3 dates is too soon (I'm out of the loop having been in a long term relationship for the past 3 years, and I also haven't felt this way around other people as I do her), but I asked her out near the climax of our evening. I wasn't actually expecting her to say yes because I understand her situation, but I was hopeful nevertheless. Anyway, I had to be blunt with her and said "Is that a no?" and she said "Yes", but she didn't sound like she wanted to.

I think dating can be more exciting and glamorous than having a relationship with someone, especially in this scenario. I think she's enjoyed dating me secretly (only her younger sister knows) and it gives her kind of buzz. I must admit I feel the buzz too. But I've said to her it's such a shame that two people seemingly so compatible can't be together because of her (or, rather, her dad's) religious views. She's been on a few dates with Jews in the month or so we've known each other and they've either been weirdos or she's not enjoyed herself.

She's a fantastic person so it'd be a shame to not have her as a friend... But I don't know. I told her as much in a pretty deep message as I was walking home at 1am and she said that it was really amazing to hear and not many people see her the way I do.

So, yeah...

I'll probably Skype her during the week and maybe we'll talk about things then.
 
Well...first Tumblr date set up for tonight. Not sure how I feel about going out with a 20 year old but I figured there's no harm in at least meeting up once.
 
GAF, in your experience, does the whole "Friends with benefits" work? This girl I've been chasing after said she's been eyeing someone else. I'm cool with that you know, but now I see she's been complaining that she's never going to get laid. Hmm.... We're still friends and I was actually thinking about bringing this up to her. It is college after all. What do you guys think? I'm contemplating just going 'About that not getting laid thing, I have a proposition".
 
Is there some golden rule regarding asking people out that work at stores?

Always wondered this. It seems like given their job, they are kind of forced to talk to you and it makes the whole thing feel really weird and unfair for them. Not to mention the fact that a lot of the time, the charm or pleasant attitude they have is most likely not genuine.

I've asked out women who were at work. I only asked them out if we had a good chat. The worst I have gotten is a no (well being in a relationship were the excuses). When that happened, I changed the conversation to something else. It's only a big deal if you make it one. So ask away, no harm in doing so.
 
GAF, in your experience, does the whole "Friends with benefits" work? This girl I've been chasing after said she's been eyeing someone else. I'm cool with that you know, but now I see she's been complaining that she's never going to get laid. Hmm.... We're still friends and I was actually thinking about bringing this up to her. It is college after all. What do you guys think? I'm contemplating just going 'About that not getting laid thing, I have a proposition".
That's guaranteed to get you not laid.
 
Well, I knew things were too good to be true with the Jewish girl. For the record, I already knew the score...Her dad's pretty controlling and doesn't want her to be in a relationship with a non-Jew and she's even sort of got it ingrained that she has to continue the Jewish line etc, even though her younger sister and older brother don't give two shits about it. She feels singled out or that her dad will come down heavy on her (well, he's basically said as much) if she starts seeing a non-Jew seriously.

Our dates have been fantastic - we've both really enjoyed each other's company, she totally digs me, I totally dig her, she's cool and intelligent, she thinks I'm hilarious, and she loves my eyes and smile. On our first two dates drink was always involved and we'd started making out towards the end of the evening like it was our first time or something. It was exciting. She even said after our second date that we couldn't keep doing this and she didn't know if she truly liked me because she wasn't completely sober. So I just gave a non-caring answer like "If you think it's best we don't continue seeing each other, I totally understand".

So a week or so later we have a 3 hour Skype call. I ask her out for dinner on Saturday and she agrees. Then she starts trying to justify herself by going on about how she finds me really fun to be around and she that she won't drink this time.

So Saturday comes around (last night), we go to dinner, have a right old laugh in the restaurant. She always stares at me uncontrollable, so I reciprocate. She says she finds my stare quite powerful. She also can't hold her shit together when I start staring and smiling at her, which I find cute.

A few minutes before we left the restaurant, she started going all coy. I tried to get her to spill the beans, but she wasn't biting. When we did leave the restaurant, she got right in my face, looked at me innocently, and started moving her face closer to mine. So we started kissing again - but this time we're completely sober (ok, I had 1 glass of wine, but she had been drinking water the whole time). Then I said "We should probably go somewhere better than standing in front of the restaurant entrance". She started giggling uncontrollable again and we went round the corner into Hyde Park.

She eventually told me why she went all coy before, and it was because she felt butterflies for the first time [with me] as I stared into her eyes in the restaurant. We found some deck chairs (lol) and just sat down talking about stuff for ages, getting cosy, laughing like children at the funny noises the ducks were making, and kissing.

Now, I wouldn't have done this if she didn't mention the 'butterflies' things and in hindsight maybe 3 dates is too soon (I'm out of the loop having been in a long term relationship for the past 3 years, and I also haven't felt this way around other people as I do her), but I asked her out near the climax of our evening. I wasn't actually expecting her to say yes because I understand her situation, but I was hopeful nevertheless. Anyway, I had to be blunt with her and said "Is that a no?" and she said "Yes", but she didn't sound like she wanted to.

I think dating can be more exciting and glamorous than having a relationship with someone, especially in this scenario. I think she's enjoyed dating me secretly (only her younger sister knows) and it gives her kind of buzz. I must admit I feel the buzz too. But I've said to her it's such a shame that two people seemingly so compatible can't be together because of her (or, rather, her dad's) religious views. She's been on a few dates with Jews in the month or so we've known each other and they've either been weirdos or she's not enjoyed herself.

She's a fantastic person so it'd be a shame to not have her as a friend... But I don't know. I told her as much in a pretty deep message as I was walking home at 1am and she said that it was really amazing to hear and not many people see her the way I do.

So, yeah...

I'll probably Skype her during the week and maybe we'll talk about things then.


This is such bullshit. I will never understand why men latch onto women who do this. She KNOWS she's got you by the balls and thus can get whatever she wants from you AND whoever else she's dating and when she's bored she can drop you and go on about her merry way. And YOU'LL STILL CALL. God, I don't mean to attack you personally but I hate seeing guys get swallowed up in this bullshit.
 
This is such bullshit. I will never understand why men latch onto women who do this. She KNOWS she's got you by the balls and thus can get whatever she wants from you AND whoever else she's dating and when she's bored she can drop you and go on about her merry way. And YOU'LL STILL CALL. God, I don't mean to attack you personally but I hate seeing guys get swallowed up in this bullshit.

Yup. If she liked him enough religion wouldn't mean a thing, at least from my experience.

She's basically stringing you along as a taboo secret fling from what it sounds like, until she finds someone else.
 
So Gaf i need some advice sorta, I asked a girl who works in the store next to mine. I like her she seems to like me, we went out on a date on Thursday and had a few drinks and played pool. Felt like the best date I've ever had, now we didn't talk the day after the date and i texted her yesterday (Saturday) just to see how she was and that seemed to go well, so my main question is when do you think it would be right to hit her up and see about setting up another date. I may be over thinking things here, my last girlfriend we just hung out once a week for 3 weeks until it got serious. I don't know i feel a little lost and that may be because she is swirling around my head more than most girls and i just don't know what i should do next. Any words of wisdom will help i plan on just going with the flow an hoping it turns out well. Thanks all.
 
So Gaf i need some advice sorta, I asked a girl who works in the store next to mine. I like her she seems to like me, we went out on a date on Thursday and had a few drinks and played pool. Felt like the best date I've ever had, now we didn't talk the day after the date and i texted her yesterday (Saturday) just to see how she was and that seemed to go well, so my main question is when do you think it would be right to hit her up and see about setting up another date. I may be over thinking things here, my last girlfriend we just hung out once a week for 3 weeks until it got serious. I don't know i feel a little lost and that may be because she is swirling around my head more than most girls and i just don't know what i should do next. Any words of wisdom will help i plan on just going with the flow an hoping it turns out well. Thanks all.

I would wait until Wednesday to ask her out again, and not a moment sooner. Don't sweat her.

How did the date end? Hug, kiss? How did she seem?
 
I would wait until Wednesday to ask her out again, and not a moment sooner. Don't sweat her.

How did the date end? Hug, kiss? How did she seem?

It went well 3 1/2 hours felt like 30 mins, Hugged and went on our way. I see her on Sundays to get food so i kinda get to talked to her, im a little hungover and tired so that may be part of my problem.
 
GAF, in your experience, does the whole "Friends with benefits" work? This girl I've been chasing after said she's been eyeing someone else. I'm cool with that you know, but now I see she's been complaining that she's never going to get laid. Hmm.... We're still friends and I was actually thinking about bringing this up to her. It is college after all. What do you guys think? I'm contemplating just going 'About that not getting laid thing, I have a proposition".

I've had the FWB situation work out quite nicely. Had a lot of fun with a woman a few years back while we were both between relationships. It was really nice having everything defined in that way as it meant there wasn't any pressure and we just enjoyed things for what they were. The sex was great too. But in my case, she was the one that proposed it to me. How could I say no? :)

So Gaf i need some advice sorta, I asked a girl who works in the store next to mine. I like her she seems to like me, we went out on a date on Thursday and had a few drinks and played pool. Felt like the best date I've ever had, now we didn't talk the day after the date and i texted her yesterday (Saturday) just to see how she was and that seemed to go well, so my main question is when do you think it would be right to hit her up and see about setting up another date. I may be over thinking things here, my last girlfriend we just hung out once a week for 3 weeks until it got serious. I don't know i feel a little lost and that may be because she is swirling around my head more than most girls and i just don't know what i should do next. Any words of wisdom will help i plan on just going with the flow an hoping it turns out well. Thanks all.

Don't over think it or play games. In my opinion, waiting until Wednesday for some arbitrary reason is just silly. If you like her, just ask her. It's not going to come across as being too soon or too clingy. I've asked someone out again at the end of a first date if it has gone well.
 
I've had the FWB situation work out quite nicely. Had a lot of fun with a woman a few years back while we were both between relationships. It was really nice having everything defined in that way as it meant there wasn't any pressure and we just enjoyed things for what they were. The sex was great too. But in my case, she was the one that proposed it to me. How could I say no? :)

I see. How did she go about asking you? If it's not unheard of I might as well have a go at it. Worst that can happen is a no.
Or an awkward pause followed by a no.
 
I see. How did she go about asking you? If it's not unheard of I might as well have a go at it. Worst that can happen is a no.
Or an awkward pause followed by a no.

In my case, she did it in a text message. I think it spared her the opportunity of it being awkward. But again, asking a guy if he wants to have that kind of a relationship is probably a bit safer. What single guy is going to say no? Still, it took guts for her to initiate and she even set up our first "date" immediately as well.
 
In my case, she did it in a text message. I think it spared her the opportunity of it being awkward. But again, asking a guy if he wants to have that kind of a relationship is probably a bit safer. What single guy is going to say no? Still, it took guts for her to initiate and she even set up our first "date" immediately as well.

Huh. That's interesting. I probably shouldn't ask her through text however haha.
 
Moved out to Philly area. Gonna try to land a job here, if that does happen. I'll go out more, and ask girls out. Never really been shy of that but as I've said before it's hard when you're unemployed.

Although it is weird now, It seems like I'm the only Mexican (not including my sister, who is graciously letting me crash on her couch) around in the area. It's kind of funny.
 
met a couple real cool guys at a show this weekend, and then got to that awkward spot where they both were interested but they were friends and I needed to make a choice. so I chose neither and went home on my own. I hate that situation, because one of the two will end up with butthurt and I just prefer both of them to suffer and I'd rather duck out. nonconfrontational anymore.
 
I feel like if that's going to happen, it'll just happen naturally as both of you just go for it. Asking a person to kiss/fuck/etc with you is just really awkward.

Yeah. You'd be surprised how open my University is though. I've hanged out with people who just said they were bored asked each other if they wanted to, left together and I'm just left going "what the fuck just happened?".
 
Slightly off-topic, but I've planned to take a mini trip out to Berlin this coming Thursday till Sunday.

I'm hoping it'll somehow help with my confidence issues, especially since I'll be traveling alone for part of it before I meet up with my friends. Should hopefully be interesting!

I'll try and speak with people at bars or whatever, especially since it should be easier to do so.
 
I'm not specific on that bit.

pretend you're talking with me. which you are. ask me something that you'd actually be curious about knowing. Here, I'll even get you started. I used to work for a chemical treatment plant, then I moved to Taiwan and taught English for a while, now I'm back in America. I enjoy acting and movies, as someone who has practiced that craft.

now it's up to you to figure out what's next.
 
pretend you're talking with me. which you are. ask me something that you'd actually be curious about knowing. Here, I'll even get you started. I used to work for a chemical treatment plant, then I moved to Taiwan and taught English for a while, now I'm back in America. I enjoy acting and movies, as someone who has practiced that craft.

now it's up to you to figure out what's next.

Theater acting or independent film?
 
pretend you're talking with me. which you are. ask me something that you'd actually be curious about knowing. Here, I'll even get you started. I used to work for a chemical treatment plant, then I moved to Taiwan and taught English for a while, now I'm back in America. I enjoy acting and movies, as someone who has practiced that craft.

now it's up to you to figure out what's next.
This is a clever exercise :D Seems like you've made some extreme makeovers in your life, how come? What kind of chem plant was it? And what does treatment mean? Since you like movies, any particular role you'd like to play? What kind of movie genre would your life fit in (or which one would you like it to be?)

Theater acting or independent film?
Try phrasing it as if this thread is irl :)
 
Anyone else ever feel like they're boring/ uninteresting to talk to? If so, how did you solve it?
Do you know jokes, puns, wordplay, etc? If not, learn them. I find most dudes blow it at dating or just conversing with others because they literally do not know a single joke or can't form one while in the middle of a conversation.
 
Do you know jokes, puns, wordplay, etc? If not, learn them. I find most dudes blow it at dating or just conversing with others because they literally do not know a single joke or can't form one while in the middle of a conversation.

Here's what you do...


Ask her if she heard that Johnny Depp's making a new Pirate movie.

and when she says no.

You say it's rated "Arrrrgh!"



Corny jokes work, people.
 
Sober, I remembered too late about your first post in the thread. I wanted to answer at the time but then I got distracted by other things.
I made a huge mistake ;D

Thanks for the video, I got a good laugh out of that.

I don't want to sound like I'm defending her or that I'm trying too hard (I might be) but I feel like the situation is complicated, even though I guess for most people labeling a situation like this as 'complicated' means abandon ship. But I don't think she's playing me or playing mindgames with me since she always seems up to hanging out almost from the second I suggest something to do.

-So she was off birth control, got back on but she's still in the midst of it so she doesn't have much of a sex drive.
-I'm actually a virgin (sound the alarm) even though I pretty much got as far as I guess you can go given the circumstances (with her)
-so I'm basically fucking new to any type of relationship PERIOD so I'm kinda learning as I go along, so I'm not exactly too smart about when to and when not to do whatever
-we still have tons of fun hanging out even if it goes nowhere but I keep making it awkward because I am trying while the above is going on

You didn't sound anxious about the relationship in your post, so I assumed you were used to FWB situations.
Since it's your first experience calling her out on her behaviour may be too much of a stretch. I'd say keep doing what you are doing and learn everything you can from this experience with a clear head. A first experience/relationship shouldn't be dissected like I did. You are right it in enjoying for what it is.
As for not wanting to fuck it up, at best I can tell you a couple of impressions I have on her after reading your previous posts.
First, huge props on not complaining about her seeing other men. I don't know if I'll make things better or worst by telling you this but: 99% of the men she talks about are pure fiction. There may be one she is also seeing, at best. I've never seen or heard about a girl having more then one FWB at a time, except when maybe she has an ex-boyfriend, a FB and a guy she is "monitoring" to assess if he's going to be fit for a relationship or not. The thing is that simply girls in FWB like to keep testing you on your behaviour, to see if you are really not threatened by the presence of other men in her life or if you are hiding your jealousy because you prefer to be number 2 or 3 rather then not having a relationship at all. So cheers, I've seen older and more experienced men then you with less character to show.
Then about the birth control and the gyno telling her to restrain from sex: this is also major BS. She is telling you this and restricting herself to oral sex because she is hesitant about you and she hasn't figured you out (yet). Despite what she says, this girl has A LOT of sex drive and she is trying to controlling it by "just" giving bjs, to control you.

-she doesn't have a phone (got it stolen, can't afford another one right away) or really any reliable way to keep in touch with her so I can't do anything small like just send a text out of the blue or whatever or arrange anything in anything with less than maybe 5 days notice.

I fear this girl may be coming out of a relationship (already or soon) and she is keeping her options open telling you this bullcrap of the stolen phone. Try some experiment at her expense: do send her a message. Don't tell her anything about it, then see how she reacts. If she flips about it and calls you out on it, tell her you forgot she told you her phone was broken. If she hasn't given you her phone number, then I'm 100% sure she is playing games...which isn't necessarily a bad thing, since it doesn't look like it affects you, but it's still something to keep in mind for future reference.

-I'm really fucking poor at having anything interesting to talk about, or maybe I'm trying to avoid certain topics because they're gaming related (even if she is a bit of a gamer), which results in her doing most of the talking (I also have no good stories).

This IMO is not a problem. If you think that's the natural flow of a conversation, then that's how relationships are for you and there's nothing wrong. Don't feel like you have to put in hours of talking just because. If you would like to talk more though, and have her listening more, simply do it. Don't stress too much about being interesting, that's how people end up getting called try-hards. She is having sex with you because she is interested in you, which makes you interesting by definition.

-My plan on trying to "hang out" more often to get more chances doesn't seem to be working, that plus my well is running dry on things to talk about in the meantime. That plus maybe I should try to cool it since I feel like I've turned the creep on by not really having much social graces about anything. If you really want specifics PM me.

I think her hesitation comes from the fact that you are not threatened by other men, which means you are not needy, but that at the same time you want to be with her (doesn't matter under which label) and you want sex, which she feels is needy. So next time she tries to guilt-trip you for showing physical affection, use this line: "you want me to feel bad...because I like you?! :D"
Deliver this with a genuine laugh at her expense and I guarantee you not even the girl with the lowest self-esteem will be able to keep fighting you off like that ;D Get her on your lap and keep tickling her, put your head to rest on her chest, pinch her out of the blue, then if she stars complaining again you tell her "hey! no sex, I promised" and you start undressing her and you go for it.
One last thing: as someone who's been around japanese, vietnamese and chinese guys living abroad (I'm in Italy), I would advise you to keep in mind that westerners don't understand strength in character in the same way that Asians do. It may be one of the reasons why she can't figure you out.
 
Well, about to go on a date with someone 6 years my junior. We'll see how it goes. Really not expecting much, but I figure I at least need to put myself out there if I want to find something.

Going on a date with a stranger feels good though. There's no prior expectation and really nothing on the line. If we hit it off, we hit it off. If we don't, then all I do is call it a night. As someone who has had to deal with anxiety issues with the past, it's nice to see that I can get over them.
 
Well, about to go on a date with someone 6 years my junior. We'll see how it goes. Really not expecting much, but I figure I at least need to put myself out there if I want to find something.

Going on a date with a stranger feels good though. There's no prior expectation and really nothing on the line. If we hit it off, we hit it off. If we don't, then all I do is call it a night. As someone who has had to deal with anxiety issues with the past, it's nice to see that I can get over them.

Don't sweat the age difference. My girlfriend is 14 years younger than I am. I never thought I'd be dating someone that much younger than me but we connect so well that it really isn't an issue at all. We have more in common that I would have ever suspected and it has been an amazing experience so far.
 
Do you know jokes, puns, wordplay, etc? If not, learn them. I find most dudes blow it at dating or just conversing with others because they literally do not know a single joke or can't form one while in the middle of a conversation.

I feel like I'm a reasonably good conversationalist and it has gotten me pretty much nowhere ever, dating-wise.

Also, anyone can rehearse a few jokes relatively easily, but I think if they're starting from zero, being funny in the moment will takes a fair amount of work... and really, the work it takes overlaps a lot with just being good at conversation anyways.
 
Do you know jokes, puns, wordplay, etc? If not, learn them. I find most dudes blow it at dating or just conversing with others because they literally do not know a single joke or can't form one while in the middle of a conversation.

I can do wordplay and jokes fine, but I can't always rely on humor to get me through the whole conversation. I just want to know what I can do to keep a conversation going after the basic "how are you" and "hows (insert hobby or work here)" questions don't give me anything new to talk about, preferably something that isn't drama, because I know that you can have a conversation that doesn't involve talking about drama, and where the person looks interested in talking and doesn't look bored the entire time, and I want to know how to have those conversations.

I actually have one other question though: How does one cope with being by themselves? I don't mean like what do I do when I'm at home with nothing to do, I mean how can one be okay with being single even when people keep throwing their relationships in your face? For simplification purposes the answer "avoid those people" is not valid. I can try but it never works for long.
 
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