how to plan the perfect first date

Stop wallowing in fear and loneliness and follow my how to guide for planning the perfect first date and have a mutually great time with anyone you’re trying to impress.

You’ve met someone you’re attracted to and you want to take them out. You’ve been wracking your brain for ideas and the same old cliché of dinner and a movie is the only popping into your head. These days, there are far more options. Set fire to all of your boring conventions. Let’s explore a thoughtful, yet proper protocol for the planning and follow through of a fun first date.

Assess the Situation

The right place to start when considering how the date should go would probably be your initial place of meeting. If your potential date is someone you’ve known for a long time versus someone you’ve recently met, you’ll want to approach the situation differently.

For someone you’ve known personally for any period of time, I would recommend brainstorming a few casual, romantic, but unpresumptuous locales for your date. You want to make your romantic intentions clear and avoid the dreaded friend zone, but you also don’t want a stuffy, formal affair where you can’t be yourselves.

For someone you met at a bar and have at least had human contact with, dinner and dancing, casual drinks, clubs, or other public spaces would be your best bet. You can meet up ahead of time if you’re somewhat familiar or you can just meet at the place.

For online dating (think Tinder, Bumble, etc.), you’re better off sticking with just drinks and letting the night unfold naturally. You want to make sure you both feel safe. It should be a pretty public, reasonably occupied place to take away any fears of not being able to escape should things go badly. If either of you are crazy, the other person should have a quick and easy way to get out without causing a scene.

Awkward encounters can arise when all you’ve done is talk on the phone or over text. In person, you have to figure out if you’re compatible. Long dinners, concerts, or sporting events are far too much time to be locked into a space together for two strangers. It’s a recipe for disaster when things don’t go as planned.

List Possible Venues

Start writing down notes about places you’d like to suggest as soon as your schedule allows. Take the time to understand and appreciate your date’s personality and interests, if you’re aware of them, when considering possibilities.

If they’re into booze and dancing, find a unique night club in your city. Find something fun and different outside of the norm. Look at online event sites, read reviews, or follow my online guide for finding underground warehouse clubs to figure out a unique place to hang out and get to know each other better. People seem to loosen up socially when there’s dancing involved, so definitely suggest that if it’s something you’re both comfortable with.

If you’re both foodies, make sure it’s a restaurant that neither of you have tried. It’s great to experience quality food with someone else for the first time. Find a place that’s right in the middle of the spectrum between fine dining and chain restaurants. My first date with my longtime girlfriend was at a really romantic sushi spot called Ooka. It’s mid-tier priced, low lit, small, and intimate. This kind of restaurant is exactly the type of setting that stimulates good conversation.

For the more adventurous types, I’d recommend some completely off the wall events. In Philadelphia, there are sometimes adult science nights at the Franklin Institute. Most art museums also have weekly or monthly events that may be fun. Find a speakeasy or a dive-y music venue. Go to a local comedy club. Find outdoor street festivals, weather permitting.

If it’s just a meetup at a bar, pick a bar that serves a large variety of craft beers or out-of-the-ordinary liquors. Find a place that has an outdoor bonfire, s’mores, table games or other activities outside of just the alcohol. Finding something fun to do while you drink and talk is important to the overall experience.

Make a Suggestion

Once you’ve picked a spot that you think will work, don’t dance around the idea. Suggest it confidently to your date and say that you think it would be fun. If they’re wholeheartedly against it, then pick a different place. You want something that you’ll both enjoy, but you absolutely don’t want to fall into the trap of saying “I don’t care. What do you want to do?” This makes you seem indecisive and non-committal and it’s a huge turn-off to most people.

If your suggestion is thoughtful and represents your mutual interests, this could be a really endearing quality that the other person sees in you. You took the time to research and plan ahead and you’re showing that you care about what’s important and entertaining to them as a person.

Be Punctual

I can’t stand people who are late. If you’re going to plan a day or evening to spend time with someone, don’t show up even 15 minutes late.

Being late shows that their time is not important to you and that’s the wrong message to send to someone you like.

If anything, get there early and stake out a good spot. Being there to greet them upon arrival takes away a large bit of the anxiety that most people feel on first dates.

To really put people at ease, it’s a good idea to send a one sentence confirmation of the plans on the day of the meet. A simple text or email such as “We’re still on for tonight?” goes a long way in letting people know that you’re actually going to show up. You don’t have to write a novel, but a simple acknowledgement is meaningful.

Be Polite

These last 2 should really go without saying if you were raised by parents who taught you the importance of manners and professionalism, but I’ll say it anyway: always be polite.

Now, some may mistake politeness for weakness, but they really have nothing to do with each other. I’m confident, straightforward, and honest with everyone in my life, but I still find time to always thank people in the service industry, hold doors for fellow citizens, pick up things people drop, and say “excuse me” when I scoot past people. It’s common sense. It’s common decency.

When you’re trying to show a new person in your life that you’re worth their time, you want to present the best version of yourself. I’m not saying you have to turn from Goofus to Gallant overnight, but make an effort to put your best foot forward. This means not talking with your mouth full, not interrupting, listening to what the other person says and commenting relevantly upon the finishing of their anecdote. Conversation is a two-way street.

You’d be surprised how many people in this era spend entire dates with their eyes on their phone, ignoring social cues and existing in some disconnected, awkward state throughout their interpersonal dealings.

Don’t be one of those people. Sit up straight, make eye contact, listen, and reciprocate and you’ll come out ahead of at least half the other people in the dating pool.

Follow up with Confidence

After the date, if it went well, you’re going to be tempted to reach out immediately. While a quick check-in that you got home safely or they did is acceptable, you don’t want to spend all night texting back and forth. Part of the fun of dating is the waiting.

Either the next day or within a few days, reach out with something charming and playful. Don’t jump straight into the serious relationship talk. Pick up the phone and call. It makes you seem far more confident than a sheepish, late night text.

Remember, you’re just starting to get to know each other. It’s best to keep things casual and unintimidating, but you want your attraction to come across as well.

If they’re free that upcoming weekend, go back to step 1 and plan another fun, unique date. Chances are, if your personalities align, you’ll be in for many more dates to come.

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