Mailbag: On handling players, touchy questions & how to ask a guy out

Well well well. After that last ‘Mailbag, Uncensored’ piece that I sent out, I found myself inundated by your letters. Deluged. Flooded. Well, to the extent that bits and bytes can flood an office, that is. Still relatively dry around here.

Now, of the dozens of letters I got, not one of them adhered to the length guidelines of 5-10 lines. Novellas and full-length sagas all around.

People! The story doesn’t have to begin in the 5th grade, when little Johnny teased you about your frilly pink shoes and you’re still not over it. Summarize. When you put in the effort to summarize the situation, you actually figure out a lot about what’s going on, what matters and what doesn’t. Otherwise you’re just putting all the onus of figuring out the situation on me, which is not helpful. Same with the perennial “What should I do?” non-question.

So the new guidelines: explain your situation and formulate your specific question in 250 words or less. Otherwise there’s no human way for me to get to all of them.  Awright, let’s start:

“Hi Ali,

I can’t believe I’m writing to you.  I’m a successful 53 year-old woman and I’ve had two long-term and very lovely relationships since I’ve been divorced.  However, over the last three years I’ve been bumping up against the same issue and so I’m hoping to get your advice. 

After four or five dates with a man, how can I ascertain whether that man is sleeping with others or if he plans to only sleep with me?  I’m interested in finding a long-term relationship and I’m trying to avoid the “players.” Should I broach this subject or should I just roll the dice and try to ascertain how a man is feeling about me through his actions?  I don’t necessarily need the man to stop dating others at this early stage of a relationship, but I feel uncomfortable about being intimate with him if he is intimate with other women.  Bringing the subject up, even in a soft, encouraging, and feminine way, has not yielded a positive response. 

What I mean by that is they say they don’t wish to stop sleeping with other women.  One said, “You’re a terrific woman and very sexy, but I just can’t say that I won’t sleep with someone else.”  And so I walk away.  With respect to my  two long-term relationships, I didn’t have this conversation with both of those men, but they both seemed to be so hooked on me that I didn’t feel the need to.  Hmm.  Maybe I just answered my own question, but I’m trying to allow for the possibility that men are all different and perhaps some warm up more quickly than others.

It could be that I’m choosing the wrong men–I usually meet men online and it seems many of them feel that dating sites are a candy store.  I may be a Snickers bar, but they also want theThree Musketeers, the Hershey Bar with Almonds, etc., who may be waiting for them around the corner.  I’ve stuck to my guns thinking that a man who truly wants a relationship and not a string of short encounters will feel the same way I do, but am I wrong? 

I’d love to get your thoughts on this subject. BTW, I’ve been reading your book and I’m enjoying it, but haven’t found the answer to this question as yet. All the best, Sharon”

Sharon –

Yes, you are choosing the wrong men. Your metaphor of online dating sites as candy stores is quite apt. When you do a search and 1486 results pop up, how much stock do you put in any one of them? Well, that’s what these guys are doing.

So yes, you would do much better by meeting serious-minded men in person, through friends. There’s no way to cook a great meal with mediocre ingredients. I refer you to the Chapter 8 of The Tao of Dating, which is all about finding good men, especially the rant towards the end of the chapter on internet dating.

But what you really need to do is to make your needs clear. Are you stating in your profile that you’re only interested in long-term monogamous relationships? And why is it so difficult to broach the subject of whether the guy’s seeing anyone else that it takes 4-5 dates? I mean, this is your life, after all. And if he’s having sex with someone else besides you, that bears directly upon your health and well-being.

So for the sake of your own mental and physical health, it’s your duty to ask sometime during the first date or before, “Are you seeing anyone else? Because I’ve found that I flourish best in the context of a long-term monogamous relationship, and if that’s not what you’re looking for, that’s totally cool.” And then you know what you’re getting yourself into, vs just rolling the dice.

This is simple due diligence, along the lines of ‘Are you married’ and ‘Do you still live with your parents’. Other questions that get to the heart of the matter is “When was the last time you had sex?” and “Are you having unprotected sex with anyone?” The more comfortable you are asking the question, the more likely you are to get a useful answer. So I’d recommend getting used to asking that question so you’re comfortable with it. Your life may depend on it.


 Hi Dr Ali

I have just purchased your book and though I am only a little way in, much of the life approaches resonate with me. In many ways the things you suggest should just be ‘known’ to us, but I guess some of take longer to know it than others.

I am 38, and been single for many years. I have loads of mates in my life mainly blokes and am terrific at making bloke friends. I am driven, love my job and i know i am funny! I am curvy (wish I was less curvy to be honest), clever, independent and quick witted. I think I am a wee bit intimidating for some but have always thought that this is just me and if blokes can’t deal with the fact that I can look after myself and laugh at my own jokes, then well que sera sera. God, see your book has already helped.

Here is my ‘thing’ I cannot, just cannot put it all on the line and simply say to a guy, ‘I am interested, are you?’. I think I read signals but I am not sure that I am not reading into actions?  Failure and awkwardness are really big issues for me.

There is a guy at work. He’s younger than me (about 8 years) a wee bit geeky, a guys who builds things, dismantles bikes and cars and puts them back together. He draws and is totally without artifice. He gave me his number, we texted on and off and i found myself making excuses to be closer or to drop into his work area. I really liked who he was straight away and told him. I said I thought he was great, gorgeous and that something was telling me to spend time with him. He beamed and said he would love to!

He has been married and recently his ex has come back into his life. He appeared confused initially and then preoccupied by this ‘reappearance’ and I backed off getting to know him. Frankly he needs the space to work out if she is what he wants, and I don’t have the headspace to deal with something being there and then not, if that makes sense. So I remained friendly and chatty but put the idea of any other possibility out of my head.

I have just returned from working overseas. All of a sudden we are back to seeking each other out and have even been out to a movie and dinner (dinner was my idea but dinner his).   

I am feeling like I want to know whether there is more to this than just a mates thing. In the past I have read to much into the mates thing and it’s been pretty awful. I am reluctant to go there again. I really just want to kiss him to see if there is the chemistry or if it’s just me. Or just say I would like to get to know you as more than just a mate. In fact I almost feel like I would like to say to him, that I need some play time with bloke, to both play and break the draught and see if us can get back on the horse, and is he interested in that too?

So I guess that as an empowered, smart and generous person I should just ask but I don’t think I could bear it if I had again misread the ‘signals’, if they are signals!!!!

Arghhhhhh. Any advice???? Thanks, Bella

Any advice? Why yes – you shouldn’t mix colors with whites in the wash. And definitely turn the heat down when you do the drying, otherwise stuff will shrink.

I’m not just being an ass here. The point is, you’re not likely to get what you want unless you know what it is. When you have a well-formulated question, you’ve figured out what you want and what the impediment is, you’re looking for a solution, and you’re ready to take action. Otherwise you’re just flopping around, subject to the fluctuations of fate.

And even though you pretty much broke every rule of asking a good question, Bella – it’s not short, and there’s no question in there – I’m going to answer this one because it’s such a common issue.

Namely, communicating your wants and needs effectively.

So some of you may know that I’m a semi-serious tournament poker player. Game theory is a pretty useful tool for making better decisions in poker – and also in dating. It basically means that you run through the various actions you can take, calculate the payoff of each one, and pick the best one. When you do this, you save yourself all kinds of heartache and headache, because you get clarity.

So let’s take the example of expressing interest in someone you’ve known casually for a while. Maybe you’ve been pining for the guy for months.

Is pining fun? No, it’s not. Making out with him – or in Bella’s country, snogging him – is better than pining. And knowing for sure that he’s not interested (so you can move on) is also better than pining. Because pining is uncertainty, and there’s almost nothing that annoys the human mind more than uncertainty.

So when you express your interest clearly – say, by inviting him to spend time with you, or making it very clear that you’d be open to the idea (“So when are you going to take me out?”) – here are the two possible outcomes:

Outcome 1: He’s into it. You get yourself some good company. Payoff: better than the uncertainty of stewing in your own juices.

Outcome 2: He’s totally not into it. You’re free to move on. Payoff: better than uncertainty.

In other words, the payoff for taking action is always better than doing nothing.

If that’s the case, why do so many women (and men) choose to do nothing, thereby stewing in their own juices for years on end? Are they all bananas?

Ahh. See, humans aren’t that rational after all (read Danny Kahneman’s Thinking, Fast and Slow for a comprehensive catalog of human folly). What’s happening here is that you’re guarding against perceived loss.

Somewhere in the back of your mind, you think you’ve got a chance with this guy. And if you ask and he says no, then you will have blown that chance. You’ve destroyed that embryo of a possibility, no matter how tiny, misshapen and unlikely to thrive it was. And that’s why you don’t take action.

Well, I’ve got news for you: you can’t lose what you don’t have.

I’ll repeat that, in all caps, just to make sure you got it: YOU CAN’T LOSE WHAT YOU DON’T HAVE.

On the other hand, if you gather the courage to step outside your comfort zone and take a chance, you just might win something exciting.

So let’s get back to Bella’s case.  First of all, Bella, you can’t just be a sitting duck waiting for this guy to sort his stuff out with his ex. You need options. I refer you to the section entitled ‘The Three Man Plan’ from Chapter 9: Meet from The Tao of Dating.

Now, you are a woman. Which means that you have power – if you choose to acknowledge it. Even more so if you’re a ‘curvy’ woman, as you put it. With a smile and a well-timed hair flip, you can get almost any guy.

The subtlety comes into play in how to use that power effectively. Plopping down on his lap and playing with his tie certainly sends a message, but would scare off even the most eager bloke. On the other hand, giggling at him coyly from across the room can go on for months without any resolution.

So you want some kind of balance between the bold and the coy, between the yang and the yin, the masculine energy and the feminine energy, the “take me big boy” and the “ooh that would be nice but dunno I may be busy that night let me get back to you.”

Here’s the formula: the main dish is the yin, the feminine, the coy, the yielding. Now spice that up with some yang, some initiative, some courage. That’s how you get the party started.

“So, when are you going to ask me out?” has both of those elements. You’re taking initiative by getting the ball rolling. That’s the yang. And yet, you’re still putting yourself in the feminine, receptive position. That’s the yin. He still has to take action and take you out.

As for what to do when you’re already out with him: flirt like crazy. You know how, right? Woman are naturals at this, but briefly: this means being playfully open to physical interaction — giving lots of green lights — without actually mauling him. That way, it still looks like he’s making the move, even though you’re the crafty engineer behind it all.

The thing that will keep you from getting overenthusiastic about any one guy (besides the three-man plan) is to remember that you’re always in evaluation mode. Why would you get super-excited about a guy you barely know? The whole point of a date is to have fun while figuring out if there’s some kind of fit between the two of you. No point getting overly sentimental about something you may not end up wanting anyway.

And from me, the guy, to all of you ladies: if I’m even the least bit interested in a woman, it’s tremendously appealing when she takes the initiative to seek my company. Even if I’m not interested, my respect for her will increase. Power, gracefully wielded, is hot.

So: take a risk. Use masculine yang energy but stay in feminine yin energy. Keep your head about you, and have fun with it!


Dr Ali B

PS: If you want a more comprehensive approach to learning all of these concepts, I recommend my 6-week course called Project Irresistible: Your Happiest, Healthiest Love Life in 2012. I expand on all of these topics and assign exercises to do over the course of each week so you actually change your behavior and get results. Use code ‘SUMMER’ to get a 50% discount.



1 Comment on “Mailbag: On handling players, touchy questions & how to ask a guy out”

  1. Ken

    Hello Dr Binazir,

    This started as a very long letter. But I’ll just give you the bare bones instead. I have kind of a weird case of “friend zone-itis” . See, we really did start out as “just friends.” We met 12 years ago when we were both starting grad school and both in committed relationships. We stayed in touch over the years through cross-country moves and relationship changes. Four years ago we ended up living fairly close to each other again and both single. We had been spending increasing amounts of time with each other and I had been falling for her more and more. When I finally got up the nerve to tell her at the beginning of this year (after dropping some hints for a year or so), I got the standard “You’re a really good friend..” stuff, as well as her telling me that “on paper” she feels we’re very compatible, but she just doesn’t feel that “spark”. And besides, (after not dating anybody for a couple years) she just met a new guy who things might out with. After staying close and talking for a couple months she disappeared for 4 months. She said she’s “been really busy”, but it’s very unlike her to minimize contact for so long. I’m certain it’s due to her overbearing BF’s feeling threatened. I’ve read a lot of dating advice in the past 4 months and want to try to create “spark” with her. (It’s amazing how much time being depressed can give you to sit and troll the internet)

    So here are the issues: 1) We really DID start out as friends, and not as potential partners. 2) I really do value her friendship. So the conventional advice of “If she doesn’t show interest, stop spending time with her and move on”. Tried it…left me very depressed and anxious. But, I’m also very frustrated being “just friends with her” while meanwhile doing all the boyfriend stuff (buying dinner, etc.) 3) While I’m trying to show her that I’m a confident, independent guy, a professional with a career I’m passionate about, good friends, and my own interests… the guys she always dates are needy and dependent losers who can’t hold jobs, often have drug or alcohol problems, and seem to need a mother more than a girlfriend. She’s never really happy with those guys and she says she wants to date the opposite. But she ALWAYS ends up with those people and she finds it difficult to break up with them once she enters a relationship. I should put in here that she’s a therapist, BTW and that she’s not a billboard model, but she is fairly physically attractive.

    Despite my trying to make a long story short, my tale of woe came out a bit overlong. But I really would appreciate any advice or insights you may have. Thanks so much.