Need Help - Dating a friend (She said yes)

[dudeman]

I (40M) have a friend (27F). We used to be coworkers. Over a year ago on a company retreat I really got to know her and began connecting with her and I noticed I caught her gaze one night. After that we went out dancing once with a group of her friends. She didn't introduce me to her friends as a friend.

I asked her out soon after, over the phone. She said she wasn't really on the market right now, but wanted to continue what we started on our company retreat (connecting intellectually and emotionally). She agreed to get together, but flaked. I was like, "Whatever." and I immediately began seeing someone else. Then my friend initiated a dinner hang out so we did and it was a disaster.

I met her quarterly for lunch after that. I was in a relationship and she would get uncomfortable if I discussed it with her. I ended up breaking up with that person and I began to see my friend more often. We go out once a month for drinks and dinner. I always pay because I am generous - with everyone; men women, whatever and she has seen this. I know she admires me as a man as she compliments me in those ways.

So 2 weeks ago I took my friend to a nice dinner and we had a great time. We flirted, touched each other playfully, and I teased her. Toward the end of our night, I told her I liked her more than as a friend and asked if I could take her on a proper date. She said, "Yeah sure, but no promises or expectations." She could tell I was about to kiss her after this as I walked to her car and she said, "Save it for the date." She later said she had a great time when I made sure she got home safe.

So I texted her the next day and set it up. An expensive Omakase restaurant which required a deposit. Yeah its expensive, but we have nice taste, I know her well, and I wanted to be a badass first date. She was excited and agreed. But the date couldn't happen for 3 weeks due to her traveling and then me traveling this week. I made the reservation.

I was completely radio silent for 2 weeks till today. I texted her, "Hey stranger. What's new in your world?" and she never replied. We don't text often, but she usually replies quickly. It has made me very anxious that she is going to flake, as she flaked before. She also may be dating other people; I'm not sure I just assume everyone is....

1. Should I preemptively cancel the date? I can find another date, but it will be a ridiculous first date. I cannot get my deposit back from the restaurant.

I was thinking of sending this text - It is a takeaway and a pretty benign neg:

So I'm feeling that vibe.... I understand if you are nervous about me and our plans. I don't want you to feel any pressure or expectation from me. Know that there are no conditions or strings attached to anything I do. I wanted to go have fun together like we always do and see if our connection could grow in a really awesome way. I have felt a romantic chemistry growing lately with you and I bet you have too. But maybe you aren't ready for this. How would you feel about canceling our date? I can make other arrangements for Wednesday. Am I wrong? What do you think?

2. Or should I just wait it out and coordinate with her what time I'll pick her up for our date early Mon/Tues?

I have played this whole relationship/situation very cool and patiently, but to come so close to getting out of the friendzone and then get denied would be unbearable. It would really hurt to get flaked on at this point and I may have to walk away from the friendship, for my own health, unfortunately.

Any advice, please? I do not want to blow this. Thanks!

 

[TheEcho]

I feel like this is above my paygrade, but I'll give it a go. Take it or leave it. Relationships exist as an arc, you want that arc to move upwards or at least laterally. Starting with a bang starts the arc very high and most likely means it will be going down sooner or later. You or her (more likely, given the heightened emotions and intuition) will feel a drop in the connection, as things aren't improving, but rather declining.

The advice to have a relaxed start to a relationship isn't just player talk or being cheap, it's to let things develop at "ground level". By starting with mostly just you two, the connection is purer and if huge flourishes are necessary for someone, well... then you aren't worthwhile to them as yourself. You can add in special things with your (presumably) partner months down the line and they will feel amazing and special, as that arcs the relationship upward from a foundation built upon "just us". As opposed to big events being necessary as they are expected part of the "foundation" if you start with going big.

As for what to do with her here? Not totally sure, though a 2 week drop off isn't the BEST thing in the world. My thought would be to cancel the big fancy date and frame it as the lack of response and wanting to start things off more naturally, less fanfare.

 

[tenere]

I see this is your first post. Mine too. Sounds like she's not interested, and keeps you on the hook for food & hugs.
Don't initiate anything else and let her come to you. If she was into you, she would have shown it by now.

 

[dudeman]

Thank you both for your responses. I appreciate it.

 

[Will_V]

I (40M) have a friend (27F). We used to be coworkers. Over a year ago on a company retreat I really got to know her and began connecting with her and I noticed I caught her gaze one night. After that we went out dancing once with a group of her friends. She didn't introduce me to her friends as a friend.

I asked her out soon after, over the phone. She said she wasn't really on the market right now, but wanted to continue what we started on our company retreat (connecting intellectually and emotionally). She agreed to get together, but flaked. I was like, "Whatever." and I immediately began seeing someone else. Then my friend initiated a dinner hang out so we did and it was a disaster.

I met her quarterly for lunch after that. I was in a relationship and she would get uncomfortable if I discussed it with her. I ended up breaking up with that person and I began to see my friend more often. We go out once a month for drinks and dinner. I always pay because I am generous - with everyone; men women, whatever and she has seen this. I know she admires me as a man as she compliments me in those ways.

So 2 weeks ago I took my friend to a nice dinner and we had a great time. We flirted, touched each other playfully, and I teased her. Toward the end of our night, I told her I liked her more than as a friend and asked if I could take her on a proper date. She said, "Yeah sure, but no promises or expectations." She could tell I was about to kiss her after this as I walked to her car and she said, "Save it for the date." She later said she had a great time when I made sure she got home safe.

So I texted her the next day and set it up. An expensive Omakase restaurant which required a deposit. Yeah its expensive, but we have nice taste, I know her well, and I wanted to be a badass first date. She was excited and agreed. But the date couldn't happen for 3 weeks due to her traveling and then me traveling this week. I made the reservation.

I was completely radio silent for 2 weeks till today. I texted her, "Hey stranger. What's new in your world?" and she never replied. We don't text often, but she usually replies quickly. It has made me very anxious that she is going to flake, as she flaked before. She also may be dating other people; I'm not sure I just assume everyone is....

1. Should I preemptively cancel the date? I can find another date, but it will be a ridiculous first date. I cannot get my deposit back from the restaurant.

I was thinking of sending this text - It is a takeaway and a pretty benign neg:



2. Or should I just wait it out and coordinate with her what time I'll pick her up for our date early Mon/Tues?

I have played this whole relationship/situation very cool and patiently, but to come so close to getting out of the friendzone and then get denied would be unbearable. It would really hurt to get flaked on at this point and I may have to walk away from the friendship, for my own health, unfortunately.

Any advice, please? I do not want to blow this. Thanks!

Attraction Has an Expiration Date

A guy meets a girl he likes. He starts talking to her, and there's electricity in the air. Attraction. He can tell she likes him. A lot, even. She tells him all kinds of things about herself, her eyes wide and filled with excitement. It feels as though there's a bubble around them, in which only...

www.girlschase.com

 

[HoofHearted]

What are you after? Sex? A monogamous relationship? It seems the later.

These are just my opinions. But both of these options run through sex anyway imo.

1. I don't think you're throwing money around effectively. I advise you to quit it. Either learn how to throw it right or keep it your pocket I say. But even if throwing it right, there's just no need, unless you yourself enjoy the lifestyle. IOW i dont believe it to be necessary to or furthering toward your goals.

2. If you want to become super simp, have sex with her first and then let her own you.

3. Part of the element of being a woman's property is being something she can show to her friends to make them jealous. This very well could be in how much she dominates you.

4. Either way, I suggest you have sex with her. The emotional effect of this could only serve you. But honestly reading it it sounds like you've had your chances and it could be too late.

5. Don't do 'dinner dates.' Btw how are you all eatin and fuckin all the time? I get indigested and sleepy, I think I would probably puke from the exertion.

6. The deposit might be a lesson learned for you. Such a classic blunder. This woman isn't committed to you. Why put yourself in this position? I get it, you have money and might not care. But philosophically an L is still an L, and I would hope that bothers you. She has a free option at the expense of loss to you. Make her pay half next time. Stop paying for shit all the time, even though it's easy for you-- because when people have to put their interests into something, it forces them to engage. Let her invest. Also, even if you're trying to flex nuts financially, this still isn't the best way.



Just some thoughts, take or leave. Good luck man, this is a head scratcher for me.

 

[POB]

So 2 weeks ago I took my friend to a nice dinner and we had a great time. We flirted, touched each other playfully, and I teased her.

Why put yourself in friendzone like that?
You NEVER EVER take women you want to fuck to nice dinner dates.
NEVER.

Toward the end of our night, I told her I liked her more than as a friend and asked if I could take her on a proper date.

Basically you are telling her:
"you should put me on hold and make me wait....I'll be here waiting while you taste all those other juicy cocks. Have a nice time with them "
Why do it?

She said, "Yeah sure, but no promises or expectations." She could tell I was about to kiss her after this as I walked to her car and she said, "Save it for the date."

See my comment above, very normal reaction from her part.

She later said she had a great time

Women are nice by nature, means nothing.

So I texted her the next day and set it up. An expensive Omakase restaurant which required a deposit. Yeah its expensive, but we have nice taste, I know her well, and I wanted to be a badass first date.

Oh boy, this breaks my heart.

She was excited and agreed. But the date couldn't happen for 3 weeks due to her traveling and then me traveling this week. I made the reservation.

Sadly, I know how this is going to end...

I was completely radio silent for 2 weeks till today.

Why?

I texted her, "Hey stranger. What's new in your world?" and she never replied. We don't text often, but she usually replies quickly. It has made me very anxious that she is going to flake, as she flaked before. She also may be dating other people; I'm not sure I just assume everyone is....

Do you really care if she's banging other dudes?
This shows very strong scarcity mentality from your part.

1. Should I preemptively cancel the date? I can find another date, but it will be a ridiculous first date. I cannot get my deposit back from the restaurant.

Take out a close friend or even someone from your family instead, have a nice time with them.
And forget about dating any girl using this type of scenario.
It's just a big shot on your own foot.

I was thinking of sending this text - It is a takeaway and a pretty benign neg:
2. Or should I just wait it out and coordinate with her what time I'll pick her up for our date early Mon/Tues?

It won't make a difference in either case.
She's gone, move on.

I have played this whole relationship/situation very cool and patiently, but to come so close to getting out of the friendzone and then get denied would be unbearable. It would really hurt to get flaked on at this point and I may have to walk away from the friendship, for my own health, unfortunately.

You are not getting close of getting out of this friendzone because all your previous actions where the reason you put yourself inside it in the first place.

Any advice, please? I do not want to blow this. Thanks!

Forget about her and improve your dating game ASAP before you commit sepuku again with the next girl.

Some pointers:
1) no more dinner dates, fancy or not. Take them to a coffeshop, bar or even deli, where you WON'T SPEND BIG MONEY ON HER. You guys can sit next to each other and have a nice one hour date, where you start the sex talk and let her open up about her sexual experiences...then you kino the shit ou of her to show sexual intent. Then you choose between the 3 bounce technique or the 2-date model, isolate and go for the kill.
(Note: most of my dates to this day have costed me between 5-30 bucks....and roughly on 20% of them I've spent ZERO MONEY....I still fucked most of those girls in the end).
2) never make plans for more than 5-7 days ahead, as the flaking chances rise exponentially.
3) never leave her hanging when texting. Radio silence is reserved for punishment, not something you use to try make yourself look cool and massage your ego. Women can smell this type of BS from 100 miles away. Learn proper texting to know how to re-engage, keep her interested and re-schedule dates.