Is Her Paying For The Date A Bad Sign? | Doc Love - Dating Advice For Men

Is Her Paying For The Date A Bad Sign?

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(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).

Hey Doc,

“The System” is great! It’s really helped me both in dealing with women and with people in my field (research immunology), for figuring out their true motives.

However, I’m having a tough time figuring out Lara, since her red flags aren’t clear. My gut tells me to forget her. I met her on She contacted me first and is five years older (33 to my 28). After several humorous exchanges she asked me if I’m as funny in person and gave me her number. I called her and we set a date.

She arrived 15 minutes early and we had a couple of drinks. She never touched me once. We laughed a lot and she seemed to be having a good time. After two hours I let her know that I had to leave since I had an early workday coming up. Not knowing her Interest Level, I walked her to her car and gave her a very brief kiss. She smiled and said goodbye.

The next day I got an e-mail thanking me for a great time. I waited four days and called her for another weeknight date. She accepted. We bowled and then went out to eat. I paid for the bowling part, but she picked up the tab at the restaurant. But still no touching. I kissed her more passionately at the end of the night. She said it was nice kissing me and I left. I got another e-mail the next day.

Now here’s the confusing part. We went out the other night again, over a week after date number two. We went ice-skating, but still no touching. She suggested drinks afterwards. We went, and she ordered food. I picked up the tab since she didn’t offer. She then wanted to go to a microbrewery. I also picked up the tab there. I kissed her at the end again. No e-mail this time.

My question is this. Is Lara a serial dater? Was her one offer to pick up the tab a smokescreen? I’m a medical resident and she has an MBA and has been working for 10-plus years, so obviously we’re in different income brackets. I find it rude that on our last date she wouldn’t at least offer to pay (red flag!), considering the bill was around $70. Also, the lack of touching bothers me.

What should I do, Doc? She does kiss and seem to enjoy it, but then again I know we don’t count anything early on. Although she has talked about the future and invited herself over to help me paint my condo, her other behavior strikes me as odd. Maybe this is why she’s still single at age 33.

Kevin - who’s straining to see the forest through the trees

Hi Kevin,

Lots of guys tell me that “The System” carries over beautifully into their business lives. And that’s because I consciously injected the principles of successful sales into dating and love, which the people who teach Psychology 101 would never think of doing.

After scratching my head over your letter, I just hope you’re clear on what a red flag is, pal. Lara went after you first, right? That happens to be a GREEN flag. She asked if you were as funny in person? That’s a personal question -- another GREEN flag. She gave you her phone number. A third GREEN flag. She didn’t turn you down when you called her for a date. I hate to tell you this, Kevin, but that’s yet another GREEN flag. Are you sure you read my stuff?

Now I’ll admit that it’s bad that Lara never touched you once. But let’s see what else she brings to the plate.

I’m going to compliment you on a couple of things here, Kevin. It was perfect that you were the one who ended the first date. You got out of there, man. Most guys would have hung around until one in the morning, and waited until the girl started yawning and brought up the fact that she had to leave because she had a busy day at work the next day.

And when you gave her a kiss at the end of the date, you CLOSED. Fantastic! Now if she’d turned her head, which would most definitely have been a red flag. But she didn’t. So all we’re seeing is green flags.

But you should have waited a little longer before calling Lara for a second date. You phoned her too soon. What’s the hurry, pal?

The woman is not supposed to pay for any of the first 10 dates, Kevin. But this girl popped for a restaurant bill. She’s a GIVER. She’s doing 99% of everything right; so don’t get hung up on the rule.

As far as the touching goes, you’re kissing her, she’s kissing you back, and she’s not turning her head. I’d rather get kissed than be touched on the arm any old day – wouldn’t you? But you’re telling yourself, “She complimented my kiss, but she didn’t touch my arm! Oh, hell, I’d better get rid of her!” Makes sense to me!

The girl’s not even supposed to offer to pay for your dates, Kevin. I don’t know where in the world you got that cockamamie idea. She already sprang for one date. Do you expect her to pay for everything? Would Cary Grant expect a girl to pay? Come on!

Kevin, you’re completely misreading what a red flag is. But you’re ticked off anyway. What did the microbrewery cost you? Thirteen bucks? Did that break you?  

Lara’s not a serial dater. Let me remind you again -- she’s kissing you. She’s going out with you every time you ask her. She’s sending you e-mails. (And when she doesn’t, you’re supposed to wait a lot longer than four days to call her for your next date. When they back off, you back WAY off.)

This woman didn’t send up a smokescreen. You’re blowing everything out of proportion. When she paid for a date, it was a good sign. You pay because you asked Lara out. If she asks you out, she pays for the date. She hasn’t done that yet.

I don’t know where your mind is, Kevin, but it was rude that you even thought about wanting this girl to pay. Count her kisses – forget the arm-touches. And next time, take her out on a cheaper date if money is an issue. But the point is this: as soon as you get out of school you’ll be making a lot of money. Heck, you’ll make what Lara makes and more. You ought to be happy that she brings down more jack than you -- but you don’t get any of it until you raise her Interest Level over a long period of time. Just wait a little longer to call her next time.

Lara offered to paint your condo for you, she kisses you goodnight, and you want her to buy meals on top of it all?

Her behavior isn’t odd at all. It’s your misinterpretation of my principles that’s the real problem here. Maybe Lara’s still single at 33 because the only guys who ask her out are guys like you.

Remember, guys: if she does 90 things right, don’t get rid of her because she does one thing wrong.

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