Stop Overthinking It – Just Talk To Her

My friend Theodore recently met a girl and wants to know how to date her in a way that will give him the best chance of forming a loving and wonderful relationship.

She’s everything he wants. Beautiful. Intelligent. Extraordinary. They’ll be perfect together – except for one minor detail: He knows practically nothing about her.

This is the stereotypical situation that many Nice Guys encounter. I’ve been there and I have some very simple advice:

Stop putting her on a pedestal and talk to her. People are deeper than a checklist of looks and an Ivy League degree. Find out if you two actually get along.

Let me elaborate:

1. Stop being so focused on looks

Who doesn’t want the hottest person they can find? But is your intention to date a mannequin or a real person? In the long run, interpersonal compatibility matters far more.

If you are having trouble dating, you probably don’t have the gift of knock-out looks (sorry) so you should focus on developing your personality. If this person really is so hot, you face some pretty stiff competition. You have much better odds trying to date someone of a similar level of attractiveness. Obviously, you shouldn’t date someone who you think is repulsive but you have to make your standards realistic.

Also, beware of the Halo Effect: People associate good looks with greatness – kindness, health, fidelity, etc. But this correlation is frequently false.

2. Dating is not an intellectual exercise

To get better at dating, you actually have to date. Yes, there will be rejections – that’s part of life.

If you have some interest in a girl, go talk to her instead of coming up with an excuse not to. Stop living in your head. Don’t waste time trying to analyze whether her dropping out of a Masters degree in theoretical physics reflects an underlying commitment issue that will result in an inevitable divorce. How can you worry about marriage when you’ve never even talked to her!? You’re not perfect so stop looking for perfection.

3. Take risks and stop worrying about whether it will work out

I know you are infatuated and really want things to work out but let’s face it – this is a stranger; more often than not, it won’t work out.

As long as you are roughly staying within cultural norms (e.g. on a first date, there’s no need to mention that you felt abandoned as a child), stop worrying about whether you’re going to offend her.

Taking no risk is actually the biggest risk of all. If you just keep staring at her from a distance and don’t talk to her (to avoid potentially offending her), you’re never going to get a date. If you do talk to her but go date after date without even holding her hand (to avoid potentially offending her), she’ll wonder if you even like her.

4. Stopping putting her on a pedestal – she’s a real person so treat her like one

Stop pre-planning everything you are going to say. If you are constantly walking on eggshells, she won’t think you sound honest or confident. If you want a long-term relationship with someone, you have to feel safe talking to them!

So have opinions. Without them, you’ll sound like a robot:

  • Girl: What kind of food do you like?
  • Guy: I like all kinds of food.
  • Girl: What music do you listen to?
  • Guy: All sorts of music.
  • Girl: Should we run or call 911?
  • Guy: I don’t know. It’s up to you.

Yes, you might offend her by saying that you like Teriyaki. But guess what, if she sees such a trivial thing as a deal breaker, she probably never liked you to begin with. On the flip side, if you offend her by revealing something that is core to your values (e.g. she is a lobbyist for an oil company and you are an environmental lawyer suing her company), this too was never going to work out in the first place.

Having said all this, during the initial stages of dating, it is a good idea to put your best foot forward. If possible, don’t volunteer too much undesirable information that is not values-related e.g. like how you leave dirty socks on the floor. The longer someone has known you, the more slack they will give you to open up to them.

5. Stop worrying that she’s your one and only chance at True Love

Such pressure just makes dating more stressful. Your real problem isn’t that you might screw this up – your real problem is that your social network is too small and/or you need to become a more desirable catch. Pursue self-improvement and do activities to improve your social skills and meet more women.

6. Do you two enjoy just hanging out and chatting?

This is a good test of whether your personalities are compatible. Their resume won’t tell you this, which is why it’s so important to actually talk to someone who you’re interested in.

If you are constantly stressing over awkward silences or worrying about whether she would be more impressed with a movie v.s. a rock climbing date, maybe you two just aren’t compatible. In order to last, relationships should feel natural instead of being a forced series of activities.

Until next time my friends, keep dating!