Sweet girl with low self esteem

[YeahWhatever420]

Hello.

I’ve been talking online to a girl who I’m sure has all the tell-tale signs of low self-esteem. She has had a couple of tough relationships and has been celebrate for a while. She puts herself down a lot, though she is very intelligent (and knows it). She may have body image issues, too.

Regardless, she is very sweet and smart and I think she is quite cute, actually. We are in the stages of messaging and calling occasionally. We have talked about meeting. She said she would like to hang out next time I’m in her town.

Its been a while since I’ve been on a proper date and I was wondering if anybody can give any tips on what to look out for (how slowly should I take things at first, anything I should avoid mentioning, any special Ps and Qs to mind when interacting with her for the first time in person)?

We started talking just as friends and so, of course, I made the mistake of telling her about some of my more wild romantic stories. Since then, she has been chiding me about being a “man-wh***”. She, on the other hand, has had very few sexual partners. Last time she jokingly asked me how im doing with “dumb h**s” on other dating sites and I did retort that I was also talking to an author I met on a dating site. We talked afterwards and the conversation was amicable.

Anyway, I get the idea that I don’t want to chat or talk too much with her, as I don’t want her to feel pressured. I also want to take it easy in person when we meet. Is this the right idea?

Thanks a bunch!

[Wiseman2]

11 minutes ago, YeahWhatever420 said:

 She may have body image issues, too. We are in the stages of messaging and calling occasionally. She said she would like to hang out next time I’m in her town. I made the mistake of telling her about some of my more wild romantic stories. 

How far away is she? When would you be able to meet? Is this the same woman?:

 

[YeahWhatever420]

28 minutes ago, Wiseman2 said:

How far away is she? When would you be able to meet? Is this the same woman?:

 

Yes. Same woman. And I travel, so the distance to her location isn’t really a big deal. She knows from our conversations, though, that in order for me to visit, I would have to put in a request to travel through there. That may add pressure that she doesn’t want, which also has me worried.

[Tinydance]

I dunno, I don't really think it's a good sign she's calling you "man w*ore" when she's actually a sex worker herself. Granted her work is only on the phone and not physically. Or were these kinds of comments were meant to be more of a joke and like teasing you? 

I think first of all you really do need to meet in person or at least video call. At this point you've never actually seen her face-to-face so I think you don't even know if she is who she says she is. Personally I don't think you need to prepare for the meeting in any way. I think it's good to just be yourself. But also why get prepared when you don't even know what she really looks like or who she is IRL yet? Definitely meet her ASAP because otherwise your crush is just getting fuelled more but you don't know how it will actually go in person. 

[MissCanuck]

This is the phone sex operator?

You would be wise to put the brakes on this. You two haven't even set an actual date, nor do you know if any of her stories about her past are true. 

In other words, you're getting really far ahead of yourself for something that might never materialize. 

[Kwothe28]

Sweet girl with low self esteem that is doing a sex phone operator work and calls you various names? Are you trying for a comedian job? Because that is a prime Netflix special material lol

You havent even met this girl and dont know if she is even real. In fact when you tried to meet her, she invented some BS excuse. Dont be feeding your fantasy more with somebody like that. You are just wasting your time. 

[Wiseman2]

3 hours ago, YeahWhatever420 said:

, I made the mistake of telling her about some of my more wild romantic stories. Since then, she has been chiding me about being a “man-wh***”. She, on the other hand, has had very few sexual partners. 

Didn't you start off by paying her for sex chat? This conversation seems typical for that calling you a bad boy, etc.

It seems like you're enjoying the fantasy including the fantasy of meeting up in person, being a GF etc. 

 

[Batya33]

I'm not a fan of your description and out of context since you wrote about this woman who is a sex worker.  That context is crucial.  I have the same opinion I had on your other thread.

[Andrina]

9 hours ago, YeahWhatever420 said:

Last time she jokingly asked me how im doing with “dumb h**s” on other dating sites and I did retort that I was also talking to an author I met on a dating site.

Let's just say that you did meet her and eventually became exclusive. Are you okay with her continuing her career, engaging in sexual talk for money? You can only have one longterm partner for your one precious life. Is that what an ideal, prized partner looks like to you, or are you desperate and overlooking it right now? If she is cute, smart, and sweet, why do you think she is single? And if you're reasoning it's because she's been avoiding relationships because of emotional baggage, then a person like that is not dating material. You're not the white knight who will be the special one to "save" her.

I did OLD for several years when I was single. As per what I quoted, it's far wiser when you're not exclusive with someone to have a "Don't ask, Don't tell" rule. You have to assume someone could be chatting with, or going on dates with others, but it's not at all pleasant to hear about that. There's absolutely no good reason to divulge that. 

What is the available times you have to date a woman locally? How often are you home versus gone for your job?

[YeahWhatever420]

Wow. Eight replies and NOT ONE could actually answer my question. Could only give me their poorly informed reasons to not pursue? Just a bunch of scolds here lol. Thanks for nothing.

[Tinydance]

1 hour ago, YeahWhatever420 said:

Wow. Eight replies and NOT ONE could actually answer my question. Could only give me their poorly informed reasons to not pursue? Just a bunch of scolds here lol. Thanks for nothing.

Well I actually said that you should meet her and you should do it soon. I just don’t think you need to do anything special because she's "shy". If you meet in person and you have attraction or connection to each other, she should feel comfortable with you regardless. 

I don't feel that it's any of my business if you want to date a sex worker. I'm bisexual so I actually did go on a date with one girl who was a sex worker and sugar baby lol It didn't go anywhere but that wasn't because she was a sex worker. By the way I wasn't actually her client, we met at a bar. I also kissed a different girl who was a sex worker. 

I actually don't mind if my partner used to be a sex worker but the key word being *used*. I don't actually want to be with someone who is sleeping with other people, whether it's their job or just in general. I think I did actually change my mind on that after I went on a date with that girl.

I'm just wondering why you haven't actually met this girl? I don't think it matters if she's a sex worker or not just in terms of why is she not meeting you in person? Even if she wasn't a sex worker but you're talking to a woman for so long and she doesn't actually want to catch up. I would personally focus more on that. If she was serious about actually meeting then surely she'd organise it? You're very keen on her so I'm sure it's not you who is putting it off.

[YeahWhatever420]

1 hour ago, Tinydance said:

Well I actually said that you should meet her and you should do it soon. I just don’t think you need to do anything special because she's "shy". If you meet in person and you have attraction or connection to each other, she should feel comfortable with you regardless. 

I don't feel that it's any of my business if you want to date a sex worker. I'm bisexual so I actually did go on a date with one girl who was a sex worker and sugar baby lol It didn't go anywhere but that wasn't because she was a sex worker. By the way I wasn't actually her client, we met at a bar. I also kissed a different girl who was a sex worker. 

I actually don't mind if my partner used to be a sex worker but the key word being *used*. I don't actually want to be with someone who is sleeping with other people, whether it's their job or just in general. I think I did actually change my mind on that after I went on a date with that girl.

I'm just wondering why you haven't actually met this girl? I don't think it matters if she's a sex worker or not just in terms of why is she not meeting you in person? Even if she wasn't a sex worker but you're talking to a woman for so long and she doesn't actually want to catch up. I would personally focus more on that. If she was serious about actually meeting then surely she'd organise it? You're very keen on her so I'm sure it's not you who is putting it off.

Hey. Thanks, Tinydance. Sorry, I overlooked your comment when I was browsing all the other less helpful and more judgmental ones 🙂

No, I don’t mind that she is a “sex worker”. That is a big umbrella term, though, which can encompass a lot of different jobs. I think phonesex operator is closer to a romance novelist than it is to, say, a webcam performer.

I live over-the-road as a trucker and am in her town probably only once every month, and often just driving through. So, that complicates meeting a little. Also, I had to wonder if this was some kind of scam (as other posters had suggested).

She has told me she would like to hang out in person, though, next time I come through. She has told me she is painfully shy in person and I think she is really uncomfortable with making arrangements. I believe she is very much looking for the take-charge type of man. Even with phone calls (unpaid, off-site), I have been the one to initiate the call, but she has stayed on the line with me for over an hour, and left it to me to end the call.

I think the “man-wh***” comments are her way of teasing, but I’m worried there is some truth in her joking: she is very conservative in her personal life and I have told her stories of my wilder days, when I was a bit of a MW.

I think she likes me. But I really don’t want to push her too hard. I’m worried of scaring her off. You think now is the time to suggest another meeting though?

[Tinydance]

12 minutes ago, YeahWhatever420 said:

Hey. Thanks, Tinydance. Sorry, I overlooked your comment when I was browsing all the other less helpful and more judgmental ones 🙂

No, I don’t mind that she is a “sex worker”. That is a big umbrella term, though, which can encompass a lot of different jobs. I think phonesex operator is closer to a romance novelist than it is to, say, a webcam performer.

I live over-the-road as a trucker and am in her town probably only once every month, and often just driving through. So, that complicates meeting a little. Also, I had to wonder if this was some kind of scam (as other posters had suggested).

She has told me she would like to hang out in person, though, next time I come through. She has told me she is painfully shy in person and I think she is really uncomfortable with making arrangements. I believe she is very much looking for the take-charge type of man. Even with phone calls (unpaid, off-site), I have been the one to initiate the call, but she has stayed on the line with me for over an hour, and left it to me to end the call.

I think the “man-wh***” comments are her way of teasing, but I’m worried there is some truth in her joking: she is very conservative in her personal life and I have told her stories of my wilder days, when I was a bit of a MW.

I think she likes me. But I really don’t want to push her too hard. I’m worried of scaring her off. You think now is the time to suggest another meeting though?

Well I understand that the phone sex operator is probably more like a fake persona or a character. So that actually does make sense that she could be shy in real life. I don't think she has any place to look down on you for being a "MH" in the past lol I mean, you're super accepting that she's a phone sex worker so she needs to accept you as you are as well. Surely she's not that conservative if she thinks sex work is fine? 

I know there are different types of sex work and I guess the phone one is the least physical. Because she doesn't actually do anything physical at all and people don't see her or know who she is. 

My advice would be not to leave it too much longer before meeting her in person. You seem quite attached to her and you think of this as a somewhat of a relationship. Maybe you should at least start video calling her? Is there a way you can give her prior notice when you'll be in her town? Or you don't know when you'd be coming through there?

Even if a lot of your relationship would be via phone and texting because you're on the road a lot, you still need to know the real her IRL.

[YeahWhatever420]

38 minutes ago, Tinydance said:

Well I understand that the phone sex operator is probably more like a fake persona or a character. So that actually does make sense that she could be shy in real life. I don't think she has any place to look down on you for being a "MH" in the past lol I mean, you're super accepting that she's a phone sex worker so she needs to accept you as you are as well. Surely she's not that conservative if she thinks sex work is fine? 

I know there are different types of sex work and I guess the phone one is the least physical. Because she doesn't actually do anything physical at all and people don't see her or know who she is. 

My advice would be not to leave it too much longer before meeting her in person. You seem quite attached to her and you think of this as a somewhat of a relationship. Maybe you should at least start video calling her? Is there a way you can give her prior notice when you'll be in her town? Or you don't know when you'd be coming through there?

Even if a lot of your relationship would be via phone and texting because you're on the road a lot, you still need to know the real her IRL.

She is in many ways a mystery and a contradiction (a total turn in for me). She is conservative in her beliefs and personal life, if she is to be believed, which I do as she was able to explain her views at great length and her personal story has stayed consistent. She has not been in a physical relationship for a few years and prefers to dress modestly.

Another huge turn on for me is that the nature of her work is entirely cerebral. She is incredibly gifted in her ability to speak and write, for that matter.

From the information she “let slip” in our conversations, I was able to verify that she is a real person. When I revealed to her that I had discovered who she was, she did not seem at all taken aback, as I thought she might be. I’ve thought about a video call, just to turn things up a notch before meeting, but not sure how I’d do that. I already feel very conscious of calling her, as that is something for which she charges. Then again, it doesn’t seem to bother her when I do. It has always been I who calls her, though.

Another point in that: she did tell me that at least two other callers call her for conversation on the app, though. I’m not sure how I feel about that. Maybe she is romantically interested in them or she is just that much in need of conversation or they were just able to pressure her into “being nice” to them.

And, yes, I should be able to give her a couple days heads-up, with a two day window of when I’ll be in town.

[lostandhurt]

So far it is all make believe and fantasy so don't read to much into what you think her character is like, level of self esteem or anything else.

 You want to go into the date with even expectations and get to know the real her, not the sex worker that gets paid to keep guys chatting.

 Basically treat her like any woman you were meeting for the first time and then go from there.

  Good idea or bad idea it is your to make.

 "If you see a chance then take it, find romance"

Lost

[MissCanuck]

27 minutes ago, lostandhurt said:

So far it is all make believe and fantasy so don't read to much into what you think her character is like, level of self esteem or anything else.

This was my point as well. 

You don't know her, OP. Not on any significant level. You're getting carried away. Be careful. Unless she agress to an actual date and sticks to it, there's little point trying to figure out how to approach any issues you believe she has. 

[Jibralta]

On 5/31/2023 at 11:22 PM, YeahWhatever420 said:

Since then, she has been chiding me about being a “man-wh***”..... Last time she jokingly asked me how im doing with “dumb h**s” on other dating sites

This is not a good sign, in my opinion. There is usually some truth in humor. She may have a very bitter attitude towards romantic relationships and sex.

[YeahWhatever420]

35 minutes ago, Jibralta said:

This is not a good sign, in my opinion. There is usually some truth in humor. She may have a very bitter attitude towards romantic relationships and sex.

I think you are right about that, unfortunately. It was a phonesex line where we initially met so I talked about my past experiences, some of which were pretty wild. I have been celibate for a year though I wouldn’t be sure how to mention that, if she would even believe me.

Last time we texted, she joked about “how’s Match or whatever site you use for hookups. Meet any dumb h**s lately”. I got a little defensive and told her I’ve been talking to writer I met on ther (which was true) to make her jealous. I called right after, told her I’m not a total MW, she laughed it off, and we talked for about an hour. 

[Tinydance]

16 minutes ago, YeahWhatever420 said:

I think you are right about that, unfortunately. It was a phonesex line where we initially met so I talked about my past experiences, some of which were pretty wild. I have been celibate for a year though I wouldn’t be sure how to mention that, if she would even believe me.

Last time we texted, she joked about “how’s Match or whatever site you use for hookups. Meet any dumb h**s lately”. I got a little defensive and told her I’ve been talking to writer I met on ther (which was true) to make her jealous. I called right after, told her I’m not a total MW, she laughed it off, and we talked for about an hour. 

Ummm OK. She's talking in a pretty crude way. Also why are you defending yourself? How can she pick on you for supposedly being a "man w*ore" when she's literally a sex worker! And why is she calling women "dumb ho's"? 

[YeahWhatever420]

Good question. I had thought maybe it made her jealous that I was talking to other girls online and that’s why she got a little nasty. Should I have gone on the counterattack instead? Like retort something to kind of “put her in her place”? Will that oddly move things forward toward a relationship?

[Batya33]

27 minutes ago, YeahWhatever420 said:

Good question. I had thought maybe it made her jealous that I was talking to other girls online and that’s why she got a little nasty. Should I have gone on the counterattack instead? Like retort something to kind of “put her in her place”? Will that oddly move things forward toward a relationship?

Yes if you two missed that day in kindergarten about playing nicely in the sandbox and basic good manners/common sense.  Yes, it will move things forward with a person who likes playing games and treating interactions as one ups/scorecard situations. Then the game moves forward and continues. Not if you want to interact in a healthful, common sense kind way with another human.

[Tinydance]

57 minutes ago, YeahWhatever420 said:

Good question. I had thought maybe it made her jealous that I was talking to other girls online and that’s why she got a little nasty. Should I have gone on the counterattack instead? Like retort something to kind of “put her in her place”? Will that oddly move things forward toward a relationship?

No I don't think so. How can she be jealous you're talking to other girls when she's also talking to other guys and not setting plans to meet you?

[Wonderstruck]

4 hours ago, YeahWhatever420 said:

Last time we texted, she joked about “how’s Match or whatever site you use for hookups. Meet any dumb h**s lately”. I got a little defensive and told her I’ve been talking to writer I met on there (which was true) to make her jealous.

Did you just ADMIT that you deliberately told her about the writer that you were talking to on Match in order to make her JEALOUS?

And you don't realize how bad that makes YOU look?

It's malicious, juvenile, and reeks of insecurity.

[YeahWhatever420]

19 minutes ago, Wonderstruck said:

Did you just ADMIT that you deliberately told her about the writer that you were talking to on Match in order to make her JEALOUS?

And you don't realize how bad that makes YOU look?

It's malicious, juvenile, and reeks of insecurity.

Yeah, actually. She was sticking her nose in my business in an insulting way, so I gave her a little taste. More importantly, she values intelligence and was insinuating that I only date or can only get “dumb h**s”, so I wanted to let her know that intelligent women are among my preferences and options. I care about her opinion of me, after all, not yours. 

[Batya33]

31 minutes ago, YeahWhatever420 said:

Yeah, actually. She was sticking her nose in my business in an insulting way, so I gave her a little taste. More importantly, she values intelligence and was insinuating that I only date or can only get “dumb h**s”, so I wanted to let her know that intelligent women are among my preferences and options. I care about her opinion of me, after all, not yours. 

This doesn't sound like a healthy way to interact at all -and  this is before you've even met? Why bother?