Sounds like a proper courting. He wants to impress, let him. You are under no obligation for sex. I say, go, have fun. Live a little.

Inn at Little Washington? Is he a foodie who has always wanted to go there, but didn't want to go alone or with a friend?

I probably wouldn't go, honestly. That is a LOT of pressure. I wouldn't let someone spend that kind of money on me unless we were serious.

How hot is he?

$500? Ouch. I'm going to not get laid for free tomorrow. Unless you count the per diem on the mortgage payment, car payment, utility bills, etc. Then I'm out more than I care to think about.

Sounds like he hasn't had any in a long time and is hoping for a little something something bang bang.

I got flowers and a funny card with a penis drawn in it so I know what to expect.

Be sure your pubes are shorn!

Anonymous wrote:How long have you been dating? You've never kissed and he's taking you out to $500 dinners.

This guy must be desperate

How long have you been dating? You've never kissed and he's taking you out to $500 dinners.

$500!!!!

You better be giving it up sister. Bring your kneepads

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:It could end up costing that with the place he chose! We've never even kissed! I'm not sure how I feel about this...

Guy here. Is he paying in full or are you splitting the bill? If he's paying and he picked it, just follow his lead with how much he's willing to spend. If you're splitting the bill and finances are a concern, then suggest a less expensive alternative. And just because he's dropping $500 on dinner, don't feel obligated to sleep with him.

Agree with this, but dont be surprised if he expects you to and get pissed if you dont. Also, please do NOT get drunk DONT invite him back to your place/or go to his if you do not plan to putting out. Have fun. Is the place Fiola Mare?

First of all, you're not getting to $500 without wine, so let's at least assume that OP will be at least slightly impaired. Know this going in OP. Have a plan. How far do you want to go? I would say that for valentines dinner, whether it's $500 or $50, you should at least lean in and give him some lip lock.

Anonymous wrote:

Anonymous wrote:It could end up costing that with the place he chose! We've never even kissed! I'm not sure how I feel about this...

Guy here. Is he paying in full or are you splitting the bill? If he's paying and he picked it, just follow his lead with how much he's willing to spend. If you're splitting the bill and finances are a concern, then suggest a less expensive alternative. And just because he's dropping $500 on dinner, don't feel obligated to sleep with him.

Agree with this, but dont be surprised if he expects you to and get pissed if you dont. Also, please do NOT get drunk DONT invite him back to your place/or go to his if you do not plan to putting out. Have fun. Is the place Fiola Mare?

Anonymous wrote:It could end up costing that with the place he chose! We've never even kissed! I'm not sure how I feel about this...

Guy here. Is he paying in full or are you splitting the bill? If he's paying and he picked it, just follow his lead with how much he's willing to spend. If you're splitting the bill and finances are a concern, then suggest a less expensive alternative. And just because he's dropping $500 on dinner, don't feel obligated to sleep with him.

#humble brag

he's expecting buns, hun.

It could end up costing that with the place he chose! We've never even kissed! I'm not sure how I feel about this...