Ask Him: How Do I Deal With Intimidating Dates?

Q: I have been hitting Tinder hard lately, and as a result I have gone on a few dates. Some of the guys I have been going out with are very locked in and successful, career-wise. They’re doing what they love, and they’re successful at it (at least according to what they’ve told me — I haven’t done background checks or anything… yet). I know it shouldn’t, but this intimidates me. How do I deal with and get past that?”

christian grey

uh oh uh oh uh oh, oh no no.

A: Oh man, this is interesting. I bet that when you started experimenting with Tinder you never thought you’d feel as though you did not have the upper hand.

Whenever I feel intimidated by something, I find that it’s often helpful to take a step back and look at the situation or subject of your intimidation in an objective way. Just take a deep breath and consider your sitch. Unless he is some kind of asshole or extreme chauvinist or insufferable douche, a man does not want you to be intimidated by him on your first date or any other subsequent dates. Or, really, ever. Intimidation a lasting romance doth not make. Write that down.

It isn’t negative that you’re having these feelings, but it is unnecessary. You’re probably having them because you’re an ambitious person, much like the guys you’re dating probably are if they’re in a great and successful professional spot. If you were to tell him about your intimidation (which there is no harm in doing), he would probably laugh it off and insist that you not be intimidated by his career — hopefully while he pours you a glass of wine from one of the house’s most expensive bottles. But he’ll probably also admire it in a strange kind of way. See, if a dude is ambitious about his career, and you’re intimidated with the success he’s had, it indicates that wherever you are currently is not a position you’re satisfied with — that you’re an ambitious person as well. And ambitious people are very attractive to other ambitious people. You get to feeling like the two of you can bump uglies then go out and take over the f**king world, one promotion or entrepreneurial pursuit at a time.

I get that you want to be on his level professionally, but just because you aren’t when you meet doesn’t mean that the two of you don’t have a great deal in common, or that you don’t share the same values. And it doesn’t meant that you should feel inferior to him or less intelligent. Some people are in positions where they can bloom earlier than others. Some figure out what the hell it is they want out of their professional life and set a straight course to it at a young age. Others take years and years to figure out what it is they really want to dedicate at least 40 hours a week to. That’s just the way it works. (I’m still waiting to bloom myself.)

Another thing to consider is that some of the reasons you may be intimidated are virtually non-existent in today’s society. There is less of a separation (at least to my eye) between social classes and cliques than there has ever been before. Sometimes I bond with rich people, with super-successful people, and other times I bond deeply with cats who are content to have as much fun as they can while working as a barista until something else happens to come along.

At the end of the day, you should be worried less about his career success than most other things, like social issues and how well your schedules can mesh to see each other on the regular.

Good luck. Don’t be intimidated.

And never go lightly to the Tinder application.

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