Suggestions for Unattached Men II – Getting Lots of Dates and Flirting

I normally write about climate change, peak oil, sustainability, and so on, but occasionally I write a personal post. Suggestions for Unattached Men was one such, and it quickly climbed into the list of Popular Posts, so I thought some more detailed suggestions might be welcomed. Here they are.

First, I am now married. Second, I was never a ‘ladies man,’ but I did ok. I also did a lot of research on improving my confidence and success with women – and I put that research into practice. I’ve recommended some books at the end of this post; buy them, borrow them, but read them. The most important part is doing.

What you do depends upon where you are, confidence-wise, with the ladies. My goals were:

• Get to a point where I could talk to any woman confidently
• Go out with those women out I found appealing

That’s it. Once you get to that level, you have no problem getting dates and girlfriends, although keeping them is more complicated. (See Suggestions for Unattached Men for, well, suggestions, and for insights into the female psyche.)

Building confidence

How do you get lots of dates? You ask women out, or get them to ask  you out. To be able to do that, you need self-confidence. The best way to build self-confidence is to do repeated actions that build it. Many men try once or twice and give up; you’ll be lucky to get anywhere that way, and will likely sabotage yourself later if you do.

Here are some suggestions for building confidence with women.

Speed dating

Speed dating is a great way to meet lots of women and build confidence. Here’s how it works: There are 20 tables, 20 men, and 20 women. One gender sits at the tables while the other gender rotates through, 3 minutes each. Each person fills out an anonymous card indicating the people s/he is interested in meeting. The organisers email only mutual matches. There is also the opportunity for mingling pre and post.

Speed dating helped me in several key ways:

• The volume of women I talked to in a dating context was more than I had ever done previously
• When you talk to many women like that, you start to relax a little; one of the common fears is that of scarcity of women, and as you meet dozens of available women you start to realise this fear is unfounded
• I became more discriminating (and therefore appeared less desperate and more confident); most of the women I met I was not interested in seeing further for one reason or another
• Because you actually meet the woman, if you do end up on a date there are no surprises the way there can be with internet dating – where you’re going on often outdated photos and creative descriptions. I’ve met women who seemed a perfect match because of their online profile, but there was just no spark when we met
• Practice, practice, practice: speed dating got me comfortable talking with women, even flirting. I consciously ‘tried out’ new behaviours to gauge the response

I would encourage anyone to go speed dating before internet dating. It is actually easier in many ways, and much more useful. And don’t go just once; go to multiple events. Repeated behaviour is key to building confidence.

Internet dating

I used Match, Lavalife, Veggiedate, and some that I’ve forgotten. These services are ok, but I found there are some drawbacks.

• You’re online, not IRL (in real life), and that builds your ‘clever profile building’ and ‘online chat’ skills, neither of which translate well to actually interacting with a real woman
• Conventionally pretty women (and those who come across as sexually open) get deluged with responses; unless you’re one of her first responses, your chances are slim
• As mentioned earlier, I could not predict chemistry based on a profile or even phone conversations; I needed to meet the person to see if there was any spark that made it worth going further
• Some women also have ‘clever profile building’ skills, and you may be surprised when you meet them; no full-body photos usually indicate either the woman finds it demeaning (and therefore doesn’t understand how men work) or she’s…big boned

All this said, you can and I did get lots of dates this way. The sheer volume of single women on dating sites helps relieve anxiety over scarcity.

Video dating

I lived in the U.S. while single and joined a video dating service – for a few thousand dollars. (The cost for women, I later found out, could be negotiated down into the hundreds.) Video is a big improvement over photos in gauging how attractive you find the person. Here, I mean not simply physical attractiveness but also all those little things, like her laugh, facial expressions when talking, her voice, and countless other attributes that somehow add up to chemistry.

The only real drawback after cost is that, like internet dating, the most attractive women get swamped. I once asked why I was not receiving responses to many of my requests for dates (video dating services have counsellors to help you) and the problem is volume. Some women were getting dozens or even hundreds of requests for dates, so any individual’s chances were slim.

The video dating service did offer an ‘image consultant’ that I found quite valuable. Many of my clothing preferences dated from high school (and I was in my thirties at the time), and where men mentally undress women, women do the opposite. Women do judge you by your appearance to a certain extent, and if you look like you don’t care…. Men can hardly complain, as we do the same thing.

Non-dating

If your confidence is at the level where you can talk to women and have fun with them, a great next step is to ask them to accompany you places. With all the methods mentioned above, there is no doubt that you’re on a date, with all the expectations and pressure that brings. With non-dating, it’s just two people having fun.

Suppose, for example, that you meet a woman who seems fun or interesting (or both) at a party or some other social event. Rather than ask her out on a date, say something like, “Hey do you want to do X on Saturday?” where X is play frisbee in the park with you and your friends, go for a walk by the seaside, go to a climate change presentation – whatever you are interested in and were going to do anyway.

This is a great way to take the pressure off and to allow you to be in an environment you’re comfortable in. Do NOT bring her flowers, pay her way, or otherwise do datelike things. If it goes well, then you can suggest another outing or, even better, not. Instead, say you had a great time, see her response, and, assuming she also had a good time, say something vague like “We should get together again some time.” Period. If she seems enthusiastic, tell her you’ll give her a call and get her number.

You can only do this if you are fairly confident. If you are still petrified you’ll never meet another woman if you let this one get away, and she’s perfect, do not try this. You’ll blow it.

Playing the game

And here I must go into a topic most men hate. The truth is, dating is a game. You may not like it, and you don’t have to play, but you can’t score if you don’t play. As mentioned in Suggestions for Unattached Men, women are always testing. I’m sure it’s biological and they want to see if we’re up to the test; it’s not personal. Men who fawn over women, who come across as desperate, or who appear clueless are not going to be respected.

So how do you ‘play’ and win? Several key tips:

1. Flirt
2. Behave confidently

That’s it. The suggestion above for non-dating automatically makes you appear confident and non-desperate. Here’s another suggestion for appearing confident that I have used that drives women nuts – but in a good way: Don’t ask them out at the end of a date. Simply say something like, “I had a good time. Thanks very much. Goodnight.”

The purpose of doing this is not simply to appear confident, but to give you a chance to mull the date over and decide if you do want another. Most men automatically offer another date at the end of the first one; this is predictable and weak. Don’t do it. It takes guts, but especially if things have gone well the woman will be intrigued and possibly pissed. This is good. Women do not like predictable, boring, easily manipulated men.

How to flirt with women

Flirting is also much easier than you may think, but it may also take some practice before you’re good at it. The easiest way to flirt is to poke gentle fun at a woman. For example, if she asks you if you think she looks good in what she’s wearing (which means she’s flirting with and testing you), respond that it makes her butt look just a little big. Then ask if it really is. Then say you can only really comment if you see her naked. (NOTE: Only do this if she has a nice butt and is confident about it.)

Having just said this, make sure all your flirting does not have sexual connotations, and don’t say the ‘naked’ comment in a sexual way. Say it matter-of-factly, as if that’s just the way it is, or it’s your policy.

Or let’s say you are out on a dinner date; you could joke that really she should be paying you because you’re so wonderful. Or if she’s afraid of something, agree and exaggerate the fear. “OH MY GOD, A SPIDER! I’ll call 911!”

The keys to flirting are to have fun and to get some back-and-forth going. Treat it as a game, but don’t get hyper-competitive! It’s supposed to be fun, not win-lose. Don’t say things in a sarcastic or demeaning way. You don’t have to make it obvious you’re joking – in fact, flirting works better if she’s not quite sure – but you do want to be a decent guy. If you come across as an asshole, no self-confident woman will want to be around you for long.

For example, while it is OK to poke a little fun at her fear of spiders, it is assholish to mock her accomplishments. If she gets a promotion at work, or does something that obviously matters to her, then do the decent thing and congratulate her. If she completes a 10K run*, don’t diminish the accomplishment; praise it.

Practice makes good enough

You will make mistakes. That’s a natural part of learning new behaviours. You may be too sharp in your flirting and hurt the woman’s feelings. If so, apologise, but don’t overdo it. Of course you didn’t mean to hurt her; don’t let her manipulate the situation into making you feel guilty. Women are always testing, remember?

If you don’t try, you won’t get. Think of anything else you’re good at; even if you happen to have a natural talent for tennis or video games or whatever, you had to practice to get good at it. Flirting, asking women out, and dating are no different. Try, adjust, try again.

Good luck and best wishes. If I did it, you surely can too.

* Thanks to JH for pointing out that a 10K is not a marathon.

Resources for this post

Here are some of the things that worked for me to develop more confidence with women. Online dating services like Match and lavalife will get you in front of a lot of women, but speed-dating is better.
David DeAngelo (the uppermost banner) offers an eBook that was very helpful to me and I recommend it highly. He also had CDs; I sold mine on eBay and am not sure if he offers them any more; search Double Your Dating. DeAngelo also offers a free newsletter with lots of great tips; click the upper banner to subscribe.