Too soon but have fun with it anyway?

[bmp2cpm]

Ok, I'm probably too close to this situation to think clearly, so I'm asking for your opinion.

Had a first date with a Match girl in early January. I really fancied her from the first moment. But, she told me her mother had always pushed her and her sister to marry very successful men who earn lot's of money. She told me that her and her sister followed that advice and it ended in divorce for both of them. She even mentioned how she dated after the divorce some successful finance guy in NY. I earn well by most standards, but I kind of think she's use to men that earn from 250 to 350 K or more a year.

She mentioned her last relationship guy broke up with her because she was too distant.
So, I played distant. Texted once a week. We had to cancel a second date twice, once from me and once from her.

I had almost written her off but texted her last Friday to see how she was. Her texts were more length, and a little flirty, and she starts telling me how she is planning to go to her condo in FL in a few weeks and wishes she had someone to go with her. I text back that with these single digit temperatures, I wish I was in FL.

Just had our 2nd date today, Monday. From the text and date, it seems like she “let me in”. We both have been dating other people and we shared our dating stories. Seems she tried dating another MD (ex was an MD) and it was so bad she’s sworn off MDs. I’m a pharmacist who works in Pharma. Her interest level seems very high since I texted her Friday. We had our first kiss today and it was good. We kissed quite a bit.

I feel like we click, but is the fact that she’s inviting me for a 3 day trip to FL at her condo before we had a first kiss a red flag? And even if it is a red flag, why not just take a chance, go to FL, and see if we have some fun together? It’s freezing here in PA and FL sounds like fun. Sure, I may get plane tickets and we may call the whole thing off but, but it’s not a big deal, right?

It’s just this went from me thinking I had little chance with her to her hinting “let’s go to my condo in FL every month together.”

So, should I go forward with FL and just have some fun with her?

About her: 43, 5’1”, very fit, personal trainer, and health coach, divorced from a chief anesthesiologist at a hospital, got a good deal in the divorce, doesn't worry about money, former AA flight attendant. She shares custody with a 13-yo daughter. Sometimes she seems very distant and focused with getting her career going. But on this second date, I saw aspects for her being a little needy, which I kind of like actually. She doesn’t want any more kids, but I get the impression she wants a relationship. And it is the day after Valentine’s day.

 

[CMNILS87]

Her bringing up that her parents told her to marry rich can tell you a lot. She's a gold digger lol. Probably sucked her first husband dry and is getting child support. I'm guessing you're well off as a pharmacist, probably like 120-150k/year?). That's more than most blue collar married couples make together a year and then some. most high up MDs and such are really nerdy and supplicate and roll over for hot chicks. I see fitness coach and she was a flight attendant lol? Must have really gamed that dude good or has body a of a goddess. Date her, but nothing serious. And don't fly down there to meet her on a hint maybe? Big risk, you waste money, and you have no idea of her interest or if she's gonna put out. She gets you to fly down, she knows she can probably get you to do other stuff for her too.

 

[sodbuster]

Until you bang her here, I wouldn't go to Fla..... It may have been a casual line. OR worse. I was invited down with my brother for a business meeting. The business never happened. I think the old fart just wanted someone to listen to his old stories.....

 

[bmp2cpm]

CMNILS87, Yep, I'm in that high range for a pharmacist and that's just my base. She already has plans to go to FL. Has her plane tickets and everything. All I have to do is take a couple days of vacation time and buy my tickets. I admit, I'm really smitten with this one. I didn't think she would go out with me again after the first date, which is why I played very distant. I have doubts about anything long term. I don't mind doing things for her if she does certain things for me. ;-) I just want to have some fun.

Sodbuster, I made another date with her for Saturday. I would definitely get physical with her before getting tickets to FL.

On the first date she told me she's not good with boundaries and has trouble saying no to people. She told me yesterday that she is a total people pleaser. She said her ex-husband controlled just about every aspect of her life. She left him once she caught him with a mistress.

My rebound relationship after the divorce was also an AA flight attendant. I do like the flight attendants and former flight attendents these days. Nothing like hearing them tell you "Coffee, tea, or me?"

 

[grayclif]

Curious as to why you chose discussing ex's and stuff like that on a first date. Whenever the conversation goes in that direction I try and steer it away to more fun topic , or funny occurrences in current events. Lots of laughing, touching and eye contact and drinks.

When you contacted her on the Friday you should have come sttaight and asked her to join you in an activity or on a date.

Don't go anywhere with her until you fvck her.

 

[Desdinova]

I feel like we click, but is the fact that she’s inviting me for a 3 day trip to FL at her condo before we had a first kiss a red flag?

Hard to say at this point since you don't really know her all that well.

I'd say go to Florida with her if you have the extra cash to spend on a plane ticket if she happens to pull LMR or you find you can't stand her. If things don't go the way YOU want them to go, then just leave.

If you don't have the extra cash for the ticket, don't go.

 

[pyros]

I wouldn't go.

Besides, the way she talked about it just makes me think that she is lonely, and this is THE ONLY REASON why she has told you about it. She just wants to have 'company'. It could be you, her friend Jessica or her sister.

Going there now just makes you look kind of desperate which puts you in a lower value position to her eyes (you're gonna spend money, fly somwhere etc just for the posibility of sex???) And if you go there and she denies you sex...then you'll feel upset, stupid and you will regret having gone there.

 

[CMNILS87]

@Desdinova

I'm 50/50 on that. Yea he has the extra money obviously, but taking vacation days and your time to fly down on a chance to bang her when she did/didn't "hint" And if doesn't go as planned...you waste time/money and vacation time and feel frustrated that he didn't get it in. If he was outcome independent I think he'd be good to next her and find a hot beach broad to bang, But I don't think that's the case. I still think he should wait and have fun with her when she comes back. Invite for drinks and back to his house. Cheaper and a faster filter for trainer lady. NC until she comes back from FL, when she initiates ask her out and go from there. I think he's just read too much into their conversations. And for god sake, steer away from any ex talk, if you don't derail that next time ASAP it will go on and on and on.

 

[AllDay85]

Ok, I'm probably too close to this situation to think clearly, so I'm asking for your opinion.

Had a first date with a Match girl in early January. I really fancied her from the first moment. But, she told me her mother had always pushed her and her sister to marry very successful men who earn lot's of money. She told me that her and her sister followed that advice and it ended in divorce for both of them. She even mentioned how she dated after the divorce some successful finance guy in NY. I earn well by most standards, but I kind of think she's use to men that earn from 250 to 350 K or more a year.

She mentioned her last relationship guy broke up with her because she was too distant.
So, I played distant. Texted once a week. We had to cancel a second date twice, once from me and once from her.

I had almost written her off but texted her last Friday to see how she was. Her texts were more length, and a little flirty, and she starts telling me how she is planning to go to her condo in FL in a few weeks and wishes she had someone to go with her. I text back that with these single digit temperatures, I wish I was in FL.

Just had our 2nd date today, Monday. From the text and date, it seems like she “let me in”. We both have been dating other people and we shared our dating stories. Seems she tried dating another MD (ex was an MD) and it was so bad she’s sworn off MDs. I’m a pharmacist who works in Pharma. Her interest level seems very high since I texted her Friday. We had our first kiss today and it was good. We kissed quite a bit.

I feel like we click, but is the fact that she’s inviting me for a 3 day trip to FL at her condo before we had a first kiss a red flag? And even if it is a red flag, why not just take a chance, go to FL, and see if we have some fun together? It’s freezing here in PA and FL sounds like fun. Sure, I may get plane tickets and we may call the whole thing off but, but it’s not a big deal, right?

It’s just this went from me thinking I had little chance with her to her hinting “let’s go to my condo in FL every month together.”

So, should I go forward with FL and just have some fun with her?

About her: 43, 5’1”, very fit, personal trainer, and health coach, divorced from a chief anesthesiologist at a hospital, got a good deal in the divorce, doesn't worry about money, former AA flight attendant. She shares custody with a 13-yo daughter. Sometimes she seems very distant and focused with getting her career going. But on this second date, I saw aspects for her being a little needy, which I kind of like actually. She doesn’t want any more kids, but I get the impression she wants a relationship. And it is the day after Valentine’s day.

Total gold digger. WITHOUT QUESTION.

Spin plates and wear a condom with this one.

PLEASE stop reading into her so much. She's sick and playing games. She'll never change.

You're so much better than this.

 

[bmp2cpm]

Curious as to why you chose discussing ex's and stuff like that on a first date. Whenever the conversation goes in that direction I try and steer it away to more fun topic , or funny occurrences in current events. Lots of laughing, touching and eye contact and drinks.

When you contacted her on the Friday you should have come sttaight and asked her to join you in an activity or on a date.

Don't go anywhere with her until you fvck her.

The topic of our ex-spouses just came up. We were both married for a long time. It didn't seem to derail things with her. I think it helps us understand each other a bit more. She typically brings up the exes.

I'm set for a date with her this Saturday. If nothing happens Saturday, then no I won't go to FL.

 

[bmp2cpm]

I wouldn't go.

Besides, the way she talked about it just makes me think that she is lonely, and this is THE ONLY REASON why she has told you about it. She just wants to have 'company'. It could be you, her friend Jessica or her sister.

Going there now just makes you look kind of desperate which puts you in a lower value position to her eyes (you're gonna spend money, fly somwhere etc just for the posibility of sex???) And if you go there and she denies you sex...then you'll feel upset, stupid and you will regret having gone there.

Very good point. I hadn't considered that.

 

[bmp2cpm]

Total gold digger. WITHOUT QUESTION.

Spin plates and wear a condom with this one.

PLEASE stop reading into her so much. She's sick and playing games. She'll never change.

You're so much better than this.

I suppose you are right, but she's really cute and I think if I go into this with no expectations or anything long term, I'll be OK.

 

[grayclif]

I'm set for a date with her this Saturday. If nothing happens Saturday, then no I won't go to FL.

Sit next to her at the bar or in a booth. Do not sit across from her. Lots of kino. Touch her hands, squeeze her upper arm and caress her her back If in jeans squeeze inside her thighs and if she is receptive to this go for a kiss. Try not to wait to the end of date to go for kiss. Get that kiss in early. It will help your confidence for the end of date kiss or if you decide to push for more. ZFG.

 

[BeExcellent]

It doesn't bother me that you guys talked about ex-spouses and that sort of thing. When you are married a long time it represents a serious segment of time in your life and so it's part of the fabric and it's common ground you can connect on (to a point - don't be someone's emotional dumping ground and don't make her yours either)

I disagree with AllDay and Pyros about the golddigger thing. She was taught what her mom taught her. She went with it and it was doing fine presumably and was loyal until she caught her husband with his mistress. To me that is a legit reason to leave the marriage. What if you caught your wife cheating? The guys here would crucify you if you didn't leave under those circumstances.

A pure gold digger would have looked the other way and stayed married to the MD to stay in that lifestyle or just replaced him with another MD straight away. This woman hasn't done that. It sounds as though she is actually questioning the way she was raised now that it has gone badly for both her and her sister. Perhaps she is disillusioned. She is used to a white collar life (and can afford it herself - again as a result of his infidelity - oh well) and I don't see that as an issue. And her having dated another MD and decided not to pursue that again seems she is questioning whether such a high priority on financial means is in her best interest.

If you feel like going to FL and can afford to do so, go. You probably spend too much time working as it is. Take a trip and just enjoy it for what it is and see if you like her. I think taking a trip with someone is an excellent barometer for how well you get along. If you don't enjoy her, enjoy the beach anyway. Use some of your airline & hotel points and get a little sun.

She is in good shape, she has some market value (which she is aware of) and she likes you. You are both busy doing life. Decide if its something YOU want to do, and go do it if it pleases you. Just enjoy it for what it is for now and don't put a bunch of future fantasies in your head. It's an opportunity to see if you like her and how well you get on. If you have sex beforehand, great. If you have sex there, great, if you don't enjoy the sex or don't have any, so what? Be open to the experience if it appeals to you. Do your thing and the rest will work itself out.

 

[bmp2cpm]

Good advice grayclif and BeExcellent,

So...even on the first date she does this bizarre routine where she tells me she should date this type of man or this type of person. Seems very random. First date, I thought she was trying to qualify me and I just kind of ignored it. Second date she did it and I thought she's doing it because I wasn't aggressive enough and she wasn't sure how the date was going. She canceled the second date because of work and on a whim I asked her out for a second date the next week after I stopped contacting her.

But we texted last night, we already have the 3rd date lined up and again she in a joking way says she should date senior citizens in FL because she goes to bed a 9:30 pm every night.

Maybe it's her sense of humor. But if she has even moderate interest, should she not make statements like that? She's always telling me she should try dating this type of person or that type of person.

She said she's a people pleaser and her sister made her sign up on Match. She is certainly is not your typical online girl.

And I always get a push-pull feel from her. Like maybe she's dating to get her family's approval but isn't really into it?

Still, she she was very compliant with the kisses on the second date. Her behavior is just weird. I think I'll go forward with the 3rd date on Saturday, but I'm thinking I should bail on the FL idea.

 

[grayclif]

Good advice grayclif and BeExcellent,

So...even on the first date she does this bizarre routine where she tells me she should date this type of man or this type of person. Seems very random. First date, I thought she was trying to qualify me and I just kind of ignored it. Second date she did it and I thought she's doing it because I wasn't aggressive enough and she wasn't sure how the date was going. She canceled the second date because of work and on a whim I asked her out for a second date the next week after I stopped contacting her.

But we texted last night, we already have the 3rd date lined up and again she in a joking way says she should date senior citizens in FL because she goes to bed a 9:30 pm every night.

Maybe it's her sense of humor. But if she has even moderate interest, should she not make statements like that? She's always telling me she should try dating this type of person or that type of person.

She said she's a people pleaser and her sister made her sign up on Match. She is certainly is not your typical online girl.

And I always get a push-pull feel from her. Like maybe she's dating to get her family's approval but isn't really into it?

Still, she she was very compliant with the kisses on the second date. Her behavior is just weird. I think I'll go forward with the 3rd date on Saturday, but I'm thinking I should bail on the FL idea.

Her action, not her words, should be your guide. Have your logistics planned out before your date. Her place or your place should be a few minutes away. I want you to f-close this bro, I know how much you guys love a warm winter vacation.

 

[Huffman]

And I always get a push-pull feel from her.

In that case I would not fly. If she's giving mixed signals there's no need to be eager yourself. I'm a bit younger but I would never spend a whole weekend like this if it's not really clear you're going to have a superb time. Let's just imagine you fly there and you spend the first day outside, then dinner, some drinks, you want to kiss but she blocks, gives the push-pull and turns into a royal b1tch. You're going to sit there for DAYS, hating yourself that you're wasting your time.

Never mind the money, having a private 3 day vacation is a serious investment of time and energy.
So - one way or another - I think we can agree that it's risky. I'd instead suggest a different date which is easier for you, you can still be lovey-dovey together but it's on your terms. If you worry about the gold digging, make it cheap-ish (not super cheap though). If she doesn't go along it's a red flag.

I'd wait to see some more good behaviour from her before committing to anything substantial.

 

[CMNILS87]

Good advice grayclif and BeExcellent,

So...even on the first date she does this bizarre routine where she tells me she should date this type of man or this type of person. Seems very random. First date, I thought she was trying to qualify me and I just kind of ignored it. Second date she did it and I thought she's doing it because I wasn't aggressive enough and she wasn't sure how the date was going. She canceled the second date because of work and on a whim I asked her out for a second date the next week after I stopped contacting her.

But we texted last night, we already have the 3rd date lined up and again she in a joking way says she should date senior citizens in FL because she goes to bed a 9:30 pm every night.

Maybe it's her sense of humor. But if she has even moderate interest, should she not make statements like that? She's always telling me she should try dating this type of person or that type of person.

She said she's a people pleaser and her sister made her sign up on Match. She is certainly is not your typical online girl.

And I always get a push-pull feel from her. Like maybe she's dating to get her family's approval but isn't really into it?

Still, she she was very compliant with the kisses on the second date. Her behavior is just weird. I think I'll go forward with the 3rd date on Saturday, but I'm thinking I should bail on the FL idea.

Mixed signals bud. Bringing up this and that and how she's bringing up she's on match and joking about other guy types ....she's ****ing with you. She's covertly saying "she has options" but kind of waving it in your face. You sure as hell don't see a guy talking about that stuff over text or on a date with a possible plate, there's no need. It's assumed you're both playing the field. Either close on this 3rd date with her or scrap it.

 

[LiveYourDream]

I don't think this woman has earned such a chunk of your time yet. She certainly hasn't proven herself as worthy in my eyes. To me, she gives off the attitude of she could "take it or leave it", referring to you. She does not seem particularly excited or interested in you or spending time with you. I get more of a ''whatever" vibe from her. You are a better catch than that! Wouldn't you rather be with a woman who is excited to be with you? Why give your attention to something less than that?

Your time and attention is valuable. To me you are not treating it as such. If this woman asked you to commit to three days of being with her, where you already are, I suspect you would counter with something like, 'we will take it as it comes.'

If you are in need of a get away or some warm weather, then arrange that for yourself or go with a buddy and enjoy the ladies where you go. I think it comes across as somewhat desperate to follow this woman and her pvssy all the way to Florida, even if you do want a trip away and a warm weather break. Neither she or her pvssy are that special.

If she knocks your socks off Saturday night, than that would be a game changer. This one is not yet worthy of so much of your time and attention. If you had other active options at the moment, I think you'd be busy with those and backseat or drop this one altogether. I think you would be better served by focusing on meeting other women.

Lastly, if you do go to Florida, I suspect, your interactions with this woman will peter out very quickly thereafter. If you are going hoping to possibly create something longer than that, all the more reason to not go, in my opinion anyway.

 

[Tenacity]

bmp2cpm,

A couple of points:

- This girl is the DEFINITION of fickle chicks that I meet from online dating sites. Online dating sites have a SEA of fickle women like this, who like you one minute, go ghost the next, like you the next minute, go ghost again, etc., etc. The woman is completely off her rocker. There's absolutely nothing quality nor special about this woman, she's the typical FICKLE online dater.

- If she's used to dating guys who make $250,000 a year in NYC, understand that with cost of living factored in, if you are living in Pittsburgh and make about $100k a year then you are technically at the same standard of living as the guy making $250,000 in Manhattan, due to the very high cost of living in Manhattan.

- Do NOT plan a trip to Florida unless she's going to pay for your plane ticket. The woman is fickle, if you want to gamble losing $300 - $600 on a plane ticket for a chick that cancels at the last minute, suite yourself.

- This is a side note, but LiveYourDream, why are you on this site lol? You do realize this is a part of the Manosphere and is a pseudo-seduction site right? Assuming you are really a woman, why would you join this site? What are YOU getting out of it? I don't think your "advice" is too off base, but it's just weird that a woman is on here as active as you are and I have no idea how you are getting any type of "self-development" out of this site.