Know Your Power…Then Get Strategic About Dating

Today’s question flips the question. A woman I have interviewed and who contributes to 40:20 Vision had a question on dating as a single 40-something. Here goes!

Q. I have a fun challenge for you!  I have a single friend who is just not meeting men (and would like a relationship).  You talk to so many women, any advice?  I told her the usual:

  • Does her online dating profile actually reflect her and what she wants?
  • Has she has to make it a priority
  • Do you take every opportunity given to talk to men, flirt if you will
  • Do you put your self it a position to meet men, go where men are (billiards, boxing, whiskey tasting, finance, beer…etc.,
  • Hit up all your friends for single dudes
  • Move to a place where there are single men

What have you heard in your world?

 A. My first question speaks to what is so amazing about the woman who asked me the question. She gave some great advice on how you can meet people everywhere when you are confident in your power.

On meeting men:

“Look at every opportunity as an opportunity. There are a million opportunities. I find myself engrossed in a world of men that I could meet. And it is funny. I could have certainly talked to 3 men on the subways today that were sting near me. All you have to do is turn around and say . . . do you know what time it is and all of the sudden you are in a conversation.  Yesterday I was in a grocery store and a guy asked me a question about the eggs. Now that I am older I realize that all these men are trying to talk to me. Which is funny. Before I would have been I don’t know. Ugh.  This man was trying to talk to me when I was picking out eggs. I was cracking up…oh right. You are trying to talk to me. He was like what eggs to you buy. blah blah blah.  I could right now ask him to go get a beer if I wanted to,”

All the times people have tried to talk to me here and there and I am not even registering it. Oblivious. Once you embrace it, it is a wild power. I am telling you. I feel like I am more attractive today that I was 20 years ago. I am prettier, funnier, sexier, more interesting more alive, less oblivious, more intelligent. What is not to love about that? And yes I am at an age where I could start to get a little freaked out about getting old. But forget that. I’m going to fight it every step of the way and I refuse to stay at home and not enjoy life. I just started taking kickboxing class and I love it. Talk about meeting men, go take a kickboxing class.” – 40-something, Brooklyn, married in 30s, mom, fashion designer

My second question…Is she ttruly open to meeting people? The old “You gotta be happy with yourself before you can be open to meeting someone else” story. Sometimes you can see 40-somethings, despite their best intentions, betting a little cynical or scared. A very long post on that here:

That aside, my advice is to live your life as if you were going to be single forever. What would you do? What would your 5-year plan be? What would you do just because you want to do it? Get into that and then you will naturally have a better energy and more naturally meet people who have your same interests and values. And you are not sending out the “oh no I’m single vibe” because you are doing what YOU love.

I would also approach online dating as if it is a fun experiment. Reflect the above (the things that you are truly interested in and get enjoyment from) in your profile and make sure your list is honest (e.g. If you don’t have a PhD …why should they?). Get specific about your interests.  Don’t spend a lot of time getting to know them online…use it as a filter to meet people offline. Then have the quick meet and go from there.

There are a  few tactical things women have shared with me. Whenever you are going to meet a friend at a bar. Arrive early. Sit at the bar and order a drink. Read the paper. Whatever. Because you know you are actually meeting someone you are not awkward and nervous and you do end up talking to strangers.

Or chat with the bartender and that will lead to other conversations with people around you. To that point. find a favorite bar and get to know the bartender so you feel comfortable going alone.  You don’t have to order alcohol. Just make it a nice neighborhood restaurant with a nice bar where you can eat or have a coffee.  Just don’t make it the trendy scent bar/restaurant

I know a woman who writes for a living and she goes to restaurant bars often just to write and grab a bite to eat. She meets tons of people. They all want to know what she is doing. Then of course there are so many people working “freelance” that the neighborhood coffee shop can become a community as long as it has Wi-Fi. Just go and set up shop and you will begin to see the regulars.

There are also so many shared workspaces these days and they are often open on the weekend. You can go for dollars a day. It’s like meeting someone at work but without the complications of meeting someone at work. Often there is a theme – writing, the arts, and technology. Do your homework.

The other thing…what does she do for a living? Meet-ups for your area of interest/career are abundant and a great way to meet people. Often times the meet-ups also sponsor panels that are a great way to meet people and learn something. For example, it’s Internet week in May (in NYC). There are tons of events, panels and parties, many of them free. There are sure to be some events anyone can apply to work and or that just pique your interest. Check out the schedule. You can buy a pass for the whole week for $30.

I open this question up to others as well. It would be fun to get advice from a 20-somethings for a 40-something.

All that said…for a great sneak peek on getting strategic in online dating…here is a really great  infographic from a panel at SXSW by Amy Webb – I Used Data Analytics to Game Online Dating. And yes she did meet her husband using her approach that beat the algorithm.   Her book comes out next year (Feb. 2013) but check out the tips gleaned here).

Can’t wait for the book. A few of her highlights:

  • Don’t just dump your resume on your profile
  • Get specific about your interests but not your career
  • Hold the sarcasm for later.

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