Should He Care If She Says She Is Going Out With Someone?

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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,

I’ve been reading your articles for quite a while. First of all, I would like to thank you for what you do to help us guys in the world of dating, and also let you know that I really enjoy reading your material. It’s the most refreshing thing on the web for men.

Now here’s my question. I met a woman I’ll call Margot (because she looks like Margot Robbie) last week at a department store at a mall, and had a very engaging conversation with her for about an hour and a half. We laughed and flirted and I could tell that she was very interested and attracted to me. We exchanged phone numbers and agreed that we would both like to see each other again.

So in other words, everything was perfect...if she didn’t have a boyfriend. When I asked her if she was seeing someone, she just said yes, without going into a whole long explanation about it. But apparently she isn’t too serious with him, otherwise she wouldn’t have responded to me the way she did, right? Usually I wouldn’t pursue anyone who was in a serious relationship, but we most definitely had a strong connection, and I would at least like to follow up with Margot.

How can I ask Margot out, or find out if she is willing to leave her current relationship, without appearing arrogant? Of course I’d like to come across as confident, though, at the same time. The goal is to be able to date her, so what would you suggest in this situation to attract her even more?

Do you think I’m leaving myself wide open for rejection or to be used by Margot? And how do I avoid that?

I know this might seem very basic to you, but I could really use the help.
 
Thanks, and sorry for the long question.

Emanuel - who’s eager to find out if he really has a chance

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Hi Emanuel,

I appreciate your compliment, and the word you used was right on the money – my column is refreshing. That’s because nobody out there among all those hundreds of so-called love doctors sounds even remotely like me. And you know why? Because I’m the only one truly looking out for you guys.

So you met Margot at a mall. Great, pal – you picked up a complete stranger (a very tough thing to do that I don't recommend because the odds are WAY against it). You beat the odds. And you didn’t just ask for her phone number and got out of there, you actually built some value into your 90 minutes together. You stretched a passing encounter into a cup of coffee and a conversation that went beyond “Wow, you have a great set of legs! Wanna get together sometime and check out my etchings?”

So for you Neanderthals out there cruising the malls, don’t just go up to her and beg for her phone number. Suggest a glass of iced tea or lemonade – that’s what you want to do. Get your time in and then pitch her for the number. You’ve got to build some value when you’re in an anonymous, public place; otherwise you’re a step away from being a stalker. And Emanuel, you did it for a whole hour and a half. Great job – as long as you didn’t get carried away with yourself and tell her you were the new crown prince of Monte Carlo!

But why are you giving this beauty your phone number? When a woman punches the number into your iPhone, you have to go straight into a hard interview, just like a good, tough love cop. “So, honey -- are you going to call me? When are you going to call me? What night? Let’s set up a time right now when you’re going to dial my digits.” Because do you know what you’re likely to hear in answer to those questions? “Uh…uh…uh…uh….” Guys, women never call! Why go through all that worthless rigmarole? Don’t give her your number. To you Psych majors, once you get her phone number, beat it the heck out of there. You’ve closed the deal.

So, everything was perfect with your little Margot Robbie-look alike, except for one little glitch…that darned boyfriend. Gosh, they’re a pain, aren’t they?

My friend, the girl has to be available. I hate to have to inject such a heavy dose of truth into your life in one sentence, but she has to be available. And this girl is not available.  

When she said she was seeing a guy, you should have asked “How many guys?” You make a valid point about the strong connection the two of you had, but it’s really just a half-truth.  

Another possibility is that she’s just being disloyal, and for you that’s not a good thing. Because what makes you think she wouldn’t be disloyal to you somewhere down the line? Or, maybe she has 95% Interest Level in her turkey and she also has low self-esteem, so she’ll take attention from anybody anywhere anytime. We got all these possibilities floating around, my friend, and that’s why I train you guys to think in terms of all the variables when you’re trying to get a read on a babe. You’re in training with me to become love detectives, and with time, you guys will start thinking like the cops on Love And Order.

Emanuel, you wouldn’t pursue a girl who’s in a serious relationship with someone else because she’s not available. But your Interest Level is up in the stratosphere and your ego is all involved with Margot because she talked to you for 90 minutes, and so you’re going to act against your own common sense.

You won’t appear arrogant by trying to move in on Margot, you’ll just appear stupid. And like most men, you’re going to come on way too heavy too fast, and she’s already got somebody else!

The odds are lousy, and you should be chasing other girls.

Manny, why are you talking about rejection? You spent 90 minutes with a girl who has a boyfriend! You have to get to nine dates with her without rejection before you even entertain the idea of where you stand.

Remember, guys:  forget about them when they tell you they have a boyfriend.