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Don’t Try Too Hard to Impress Your Date

Two people on a beach on a date.

There’s no moment sadder than the moment someone blatantly tries to impress you and fails. “Depending on which economic calculation you use, I may or may not be the richest person in the world. I’m good friends with this guy who knows Bruce Springsteen. Surveys have shown that I’m the most attractive person in Michigan. Can I buy you a drink?” No. No, you may not.

Number one, you’re lying, and number two, what, am I supposed to be impressed? Ew. Can’t we just stop trying to impress one another and start being ourselves?

Obvious “I want you to find me impressive” conversation is boring, tedious, and uncomfortable. It’s also counterproductive, because if a person is truly impressive, they don’t have to talk about it. You know when you should be impressed by someone, and impressive people know that you know so all the “I’m impressive blah blah blah” doesn’t really apply. People who talk about the many impressive qualities they have also come across as ecomaniacal, self-centered, and uninteresting. All a braggart wants is an ego boost, and their behavior is transparent and annoying.

We are asked to talk extensively about ourselves when dating a new person. Part of the fun in dating is sharing stories about yourself and listening to the stories of another person. But the type and quality of your conversation can veer from being informative and inclusive to being egotistical and self-centered — without you even realizing it.  This is a risk we all run. And I know we’ve all had moments when we casually say something, and then worry that what we said might have come off the wrong way, as if we sounded boastful or pompous. And we feel embarrassed.

Here are some rules that any dater can follow to keep conversation on course and to avoid the unfortunate and often unintentional case of “I’m trying to impress you” talk.

1. Avoid talking about money too early on.

This is a classic rule of dating. As we wrote in our “What Not To Do On A First Date” blog entry last month : “Zoosk recently conducted a study of over a thousand singles all across the United States, asking about sensitive issues like dating during a recession, unemployment, and going on dates that involve free activities as opposed to dining out extravagantly.  What we found was that money can’t buy love, and that people don’t really let factors like money influence their decisions too much when it comes to dating someone they really like.” Don’t talk about money in polite company, as the old adage goes.

2. No one needs to know about complements, honors, or attentions you’ve received.

I am sure you are an impressive person, but gloating too much about the many facets of your glorious impressiveness can have the effect of making your date — or anyone — feel small and unimpressive in comparison. This causes feelings of insecurity and resentment, and will practically ensure that you won’t get a second date (unless your date decides to keep dating you because they loathe you so much, in order to one day dump you out of the blue to take you down a notch — it’s happened before).

3. Think of the 5 most impressive things about you, write them down on a list, and make a mental note not to bring them up unless it pertains to the conversation or if you are asked.

There are certain topics that are generally avoided unless you are asked. These include what your exact job title is, where you went to school, what car you drive, how cool you are, the list goes on. Write down the 5 most impressive things about yourself and make a mental note not to be the first person to bring them up in a conversation, unless it’s directly relevant to the discussion. Trust me, you’ll come off as way more impressive if you keep your mouth shut unless you’re asked (at which point you casually drop the bomb). Be off the cuff; be too cool to even care. And then gloat as you watch your date’s eyes widen in shock and then turn misty with lust.

4. Don’t be a name dropper.

Name dropping is a cardinal sin of dating. Just because you know some impressive people does not then make you impressive yourself. It just makes you a name dropper. Blatant attempts to place yourself in the social hierarchy are pathetic, and people can and do know it when name dropping happens. You aren’t pulling the wool over anyone’s eyes. Your date agreed to date you, not your random celebrity “friends” (skepticism noted).

5. Show, don’t tell.

The best policy, in dating, is to show rather than tell. This rule is almost universally applicable. Rather than telling your date about the many sides of who you are, show them. Show your date how smart you are with witty conversation and great book recommendations. Show them how caring you are by being a good listener. If you make a lot of money, treat your date to a nice dinner rather than blurting out the contents of your Roth IRA. If you have a cool talent, well, organize a talent show! It won’t be long before your date realizes what an amazing person you are, and the best thing is: you didn’t even have to tell them.

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