Brazen First Date Choices That Might Win Them Over

One of life’s most difficult social situations is the first date. Whether it’s a blind first date, or a dating site connection first date, the first social encounter with another person with a romantic journey at stake certainly disrupts nerves.

It’s natural to feel those nerves.

One part of the nervousness is the planning of the first date.

There are lots of go-to first dates, such as the coffee shop meetup, or maybe a happy hour social.

There is nothing wrong with what’s tried and true. Often, there is no reason to fix what’s not broken.

However, if you’ve been on a lot of first dates and you feel things haven’t rolled in your favor yet, you might be considering a more brazen first date choice. It is only natural to consider other options outside status quo meetups when those status quo meetups haven’t yielded the desired results.

But being bold isn’t an easy choice.

Let’s take a deeper examination of what it means to be bold on a first date and what some of those bold options might be.

It’s Risky, But That Can Be OK

Without risk, there is no reward.

We’ve heard that thousands of times.

But should we apply that to our dating site lives?

In some cases, there is nothing wrong with making a bold first date choice. But there are some risks involved.

Bold first dates often cost more

Not always, but in many cases, a more provocative or interesting date plan can cost more money. On a first date, it’s best to lower your financial and time investments. So choosing bold might ramp up your money and time spent. You just have to understand that.

Might extend date beyond comfort levels

Coffee shops are great because if upon first encounter you don’t enjoy your company, it’s easy enough to bail out. This isn’t the case if you are hiking an incline or in a plane. In those cases, you’ll be stuck roughing it out.

She/He may hate it

It may happen. If it does, the date could be ruined.

She/He may not show

Remember, first date nerves are real. If he/she is already on edge, the thought of hanging out with someone they don’t know super well in a situation that feels unfamiliar may prompt them to back out.

So now that we’ve assessed some bold first date risks, what are some options for those still reading?


In the category of bold dates, skydiving is the ultimate risque cliche. Skydiving on its own is scary and unsettling, much less with someone you barely know. If you suggest skydiving for a first date, make no mistake about it, she/he will think you are bold.


I know, you didn’t expect a concert to show up under bold first dates. But the fact is, concerts mean hours on end together with someone you don’t know. They are often relatively expensive. They also tend to run late into the nighttime hours. That’s a lot to take on with someone you barely know. Both time and money investment run high.

Anything With Your Parents

This one almost seems beyond the realm of considerations, even as it falls under the bold first date choice categories.

I could never imagine taking a first date to a place where they’d encounter my parents. That’s way too early in the process.

But maybe if you’re trying to show yourself as a family person, the bold choice pays off.

A Political Rally

Politics and first dates just don’t mix, even when both of you checked the same political boxes on your dating profile.

These days, politics are divisive. You and the single person you barely know are sure to thrust into some divisive, polarizing conversations. It’s typically better to get to know one another before holding those conversations.

Introducing Your Friends

While not nearly as awkward as a first date that involves your parents, your friend circle can be a risky first date atmosphere nonetheless.

It might make your date feel as though things are moving too fast. But if the risk pays off, maybe that’s the winning formula.


In the end, first dates are all about the feels. If you feel like making a bold choice will separate you from the rest of the dating site herd, it might be time to make such a move. Being bold is always risky, so long as you understand that up front, you won’t be let down by any fall out. Brazen first dates do have one upside, they can make you a more attractive catch.