How to Date More Effectively

Dear Karen,

I am so frustrated!  I have had three dates with a guy, and I don’t feel like I know him any better now than when we first met!  I don’t feel any connection with him, although, from what I learned about him through his profile, he’s got lots of potential.  How can I get him to stop being so superficial?  And how do I get him to tell me about his relationship background? – Jennifer, CT

Hi, Jennifer,

Thanks for this awesome question…I know there are lots of women who have felt, or feel, the same way you do.  There’s some great stuff you can do to move things along nicely.  Let’s get started!

Be What You Seek

If you’re a regular reader, you know this is a big theme in my advice to women.  If you sit back and wait, rather than just being authentically self-expressed, you’re going to either attract a man who legitimately is not a good fit, or he’ll be doing the same thing (holding back), and the potential you may have had will just die on that old (withholding) vine.

You mention that he seems superficial, that you don’t know him, and that you don’t feel a connection with him.  My question to you is this: how well are you doing at revealing yourself, and at asking him questions about himself?

Note: don’t be the “Spanish Inquisition”, with your arms crossed, running down the mental check-list of “good answer” or “bad answer”.  That would clam up any man!  Be interested, be curious, be conversational, and share your own answers to the questions you ask him.

Online Dating Invites More Honesty

One of the (many) things I love about online dating is that, unlike when you meet someone through a social activity (except for singles events, obviously), there are things that are stated right up front:  relationship status, interests, all sorts of demographics, etc., that you wouldn’t just come out and ask if you were feeling that you needed to be “polite” when meeting at a party, for instance.

What that means for you is that it’s perfectly okay to ask things like “Have you ever been married?” or “Have you ever been in love/serious with a woman?”, or “Where do you see yourself in a year/five years/20 years?” or “What do you think about women who choose to remain a virgin until they’re married?” or “What did your parents model for you, growing up?” when you’re on a date with a man you’ve met online.

The bottom line is this: you can’t have an authentic, intimate, connected relationship with a man who is a scrumptious fit for you, unless you are authentic, intimate, connected, and letting yourself be seen for all of who you are (and are not).