More Tough Love

My question revolves around approaching women on the streets. What is the ideal way of doing so? I have spoken about boring things like the weather, fascinating things like spells or cryogenically frozen heads… I have also spoken directly and simply let girls know I find them attractive. Reactions, I find are scattered. Is there an ideal way to make a girl feel safe and secure enough to give a chance meeting just that… a chance.

– F

Dear F,

I’d stay away from the frozen heads and spells. You don’t want her thinking you’re certifiable. Women naturally hesitate to speak with strange men in public places because there’s an element of vulnerability involved. We assume that they must be either insane, drunk or pervs. Unless they look like they’ve stepped out of an Abercrombie & Fitch catalogue, in which case, this rule does not apply.

So what do you do, Joe Shmoe? Go it old school. A warm, genuine smile and eye contact will disarm her, and she’ll smile back. Approach, saying you couldn’t help notice that she was pretty/beautiful/had a lovely smile, etc. and then head straight into a dialogue – about the weather, the late trains, where she got that great coat (you want to buy one for your sister, best friend), etc. – before she turns away. Try not to sound desperate, steer clear of sexual innuendoes and DON’T ask for her number. Offer yours instead, and get her to promise she’ll call you.

I met this girl online. We met last summer, went on a few dates and a trip together. I enjoyed the time we spent together: good conversations, wine and food, etc. So did she, it seemed. I wanted our relationship to be closer, and she never did give me the signals. It has been 9 months, we remain as newly met dates/friends. I stopped calling her for a period of time, then she called and wanted to get together. And it goes again. Advice?

– Confused

Dear Confused,

It’s time to have the “talk.” You can want all you want, but you aren’t going to get it if you don’t ask for it. I’m not sure I understand why you didn’t say something 9 months ago. It appears as though she could be interested in you but hates making the first move; however, her calling you after your silence could be taken for “a move,” no matter how small.

What signals were you expecting? Not all women give signals. Sometimes we keep it in our head and take it home to bed. Next time you meet, talk about how you feel. Make the moment an end of the date thing – as you walk her to her door, as you walk out of the restaurant. Don’t put her or yourself in an uncomfortable situation where you blurt out how you feel during the appetizer and spend the main course and dessert in stony silence. She sounds like she’s on the fence or uninterested. Either way, it would be in your best interest to find out.

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