Relationships Talk

Want to Plan a First Date That’ll Impress? Avoid This Common Mistake

The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch – or several. Need his help? Email askus@askmen.com.

The Question

Dear Dating Nerd,

I asked this girl out and I want to impress her because I’ve had a crush on her for a long time. Now that I have the chance, I want to treat her right. . However, I don’t have a ton of money. What’s your advice for an impressive first date? Should I splurge just to make a good first impression? Are there good date ideas that don’t cost a ton? I don’t have a ton of dating experience, and I know what to do on an  average date (dinner, movie, drinks), but those seem so boring. I want her to know she’s special. What’s your advice?

– Debating Dirk

The Answer

Hi Dirk,

First of all, congratulations on being a thoughtful young man. That quality is sadly too rare these days, I find. Seeing a guy who cares about his date’s experience and not just his own is heartening. Whatever happens on this date — whether it’s a success and leads to a long, loving relationship, or whether you flame out and she never speaks to you again — know that you’ve got your heart in the right place. Trust that  someone will see that.

Now, in regards to impressing someone on a first date, the truth is, everyone will be impressed by different things. Unfortunately, there’s no blanket advice I can give you that will definitely impress your crush. What I can give you is a few ideas, along with a set of best practices to follow.

I’ll start  by addressing your question about splurging. There’s no dating law anywhere that says you absolutely can’t splurge on a date, and rare is the woman who’s looking for a guy to spend less on her than more. Not to mention, wanting to show off a bit on a first date is a totally understandable approach.

You want to be your best self, appearing well-dressed, well-groomed, and articulate with regards to the worlds of art and commerce, all while being  capable of making your date laugh. Spending a little extra is right in line with that.

RELATED: How to Prepare for a First Date, Explained

I’d warn against that approach, however. Beyond the fact that you might not be able to actually afford the expensive date you’re planning, the issue with blowing a bunch of cash on a first date is threefold. Allow me to list them:

First, things might fizzle out due to a lack of interpersonal chemistry. First dates are notoriously tricky things to nail, and the likelihood that you’ll never go on a second date is just as good, if not better, than things working out down the road. That’s the reason most first dates these days are just two people going to a bar. Why expend energy on something that most likely won’t work out?

Second, spending more money doesn’t necessarily equate to impressing your date. Sure, brunch in a French chateau is objectively a more unique experience than hitting up a Denny’s. And yes, much of our society is trained to accept the equation more money equals a better time. In actuality, that convenient bit of math ignores the fact that your date might go against the grain and prefer cheaper alternatives, or might find upscale establishments stuffy or uncomfortable. You might be working extra shifts to make this date work only to realize you were actually shooting yourself in the foot.

Third, and probably most important, is the question of honesty. On a first date, you want to show your best self. The keyword there isn’t “best,” but instead, is “self.” You should be showing who you are, not who some imagined version of yourself is. Spending way above your financial comfort level to impress a date isn’t just bad money management, it’s also dishonest. That’s a pretty bad way to start off a courtship.

Rather than trying to impress your date with a version of yourself that’s completely (or even relatively) artificial, try to impress her with a version of yourself that’s true to you.

Pick a first date idea that lines up with who you are. It sounds like you’ve known her for a while, so hopefully you have an idea about some of her likes and dislikes by now. Do something you think she’d appreciate.

If you’re both into a certain type of cuisine, bring her to a hip new restaurant to show off your knowledge. If you’re both outdoorsy, going for a walk in a gorgeous park with some coffee. If you’re both film nerds, suggest checking out a retrospective from a legendary director playing at a nearby repertory cinema. You get the idea.

In short, you’ll impress her most by showing that you care about her having a good time, not by throwing wads of cash around. After all, if things work out between you two, it’ll be because of the things you actually have in common, not the things she thinks she has in common with a fake version of you.

You don’t want to trap yourself into having to pretend you’re someone else all relationship long.

The final bit of advice I have for you is to be flexible. After all, you’re doing all this to impress her, not yourself. As much as coming up with a cool and unique date idea is a good approach, it’ll be all for naught if that means forcing her to suffer through an evening she hates. While I definitely recommend going into your conversation with a plan in hand, it’s just as important that you remain willing to compromise.

If you propose an idea that’s very much “you” and she counteroffers with an idea that’s very much, well, not, that’s a tough feeling. But don’t panic! So long as her idea isn’t an absolute 100 percent no-go for you (and if it is, you have my permission to pass),  give it a whirl. If it pans out, you’ll have an opportunity to ask her out on a more you-styled date next time.

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