A Guy's Guide to 21st Century Dating

When it comes to success in today’s modern, online dating scene, it takes a bit more than luck and good looks. Master the dating game by putting these tips into practice.

There was once a time when the process of dating was a work of true art for men. A chivalrous male, upon seeing a woman whose beauty and personality captivated him, would set forth to invite the dame to join him for an evening of fine dining and fun. After cleaning himself up and dressing to impress, a man would venture into the relational unknown with hopes that the night would end with the prospect of a second date.

Sound a bit too romantic? If so, you can blame today’s point-and-click culture for taking the skill out of dating. For many men in the modern age, most “dating” begins online. With a few well-timed swipes, one can quickly scan through a variety of social profiles of potential mates, hoping to match with one for a conversation - or perhaps something more. Seems like online capabilities has taken the mystery out of the magic, right?

Unfortunately, many men enter into the dating scene with high expectations for immediate success, only to find those hopes dashed. For some, the idea of landing a date with a perfect match can seem nearly impossible.

If this hopeless romantic is you, dear reader, take hope! There is yet hope for you to succeed in dating in the 21st century. Here is our guide for landing a date in today’s digital-first ocean of possibilities!

But First, Some Pre-Game Pointers

Nobody wants to jump in head-first without a bit of preparation. Before you continue reading our guide for dating, here are some pointers that will help you make a great first impression when starting off your dating interactions online:

● Start Bold With Your Strengths
If you are looking to meet someone online, make sure to lead out with your greatest strengths. Nobody wants to meet an insecure and fearful man, so pick out a few strengths that others have pointed out about your character and personality, and add those to your profile. Remember - a little bit goes a LONG way online!

● Showcase Your Looks With Real & Appropriate Photography
Even if you meet someone in person, it is highly likely that the first place they will go to learn more about you is your social media profiles. Do a quick audit through your channels to ensure that you’ve put your best-looking foot forward to showcase your true looks and personality. Keep it appropriate. If that picture would give you hesitation, you can bet it will make someone else stay away as well.

● Curate Your Feed
Now, more than ever before, your social media and online dating profile is a great way for someone to learn more about you before your first date. In the same way that you audited your profile pictures, make sure your content across your channels shows the true you - your interests, your hobbies, and those cute pictures with your family and pets!

● Don't Make It Weird
Sometimes a connection seems right at first, but doesn’t go anywhere. If you have been reaching out to someone you fancy, and they aren’t returning your gestures, take the humble and high road and move along. There are many fish in the dating pool - don’t be one of the ones who can’t take a hint!

A Guide to Dating in The 21st Century!

After following the above steps to ensure that you are putting your best digital foot forward, it's time to step out and start going on dates! Many of the tips in our guide below are tried-and-true ways for you to help the date go well and increase your chances for landing a next meetup.

1. Step Out & Ask!
Unfortunately, too many men today have become passive and lazy when it comes to asking a woman out on a date - as though women will simply line up for a chance to spend time with them! Want to rise above the competition quickly? Pluck up the courage and lead with a strong, courageous ask! Even if the answer is a “No Thanks”, you will still impress her (or her friends!) by showing some intentionality!

2. Come Up With A List Of Fun Date Ideas Before You Ask
Want to really impress your date? Have a pocket full of fun ideas ready to offer up from the beginning of the conversation! In today’s competitive dating market, it’s not enough to simply ask someone to go out with you - you need to have something in mind to do! Here are our top 10 ideas:

1. Visit a museum
2. Bowling
3. Karaoke
4. Mini Golf
5. A local festival
6. A picnic
7. A comedy show
8. Trivia night at a local bar
9. Try out an Escape Room
10. Play a tourist in your city (or town)

3. Offer To Pay, & Be Willing To Let Them Pay As Well
Traditionally, the man always pays on the first date. However, as gender roles have continued to shift, it is best to always clear up this uncertainty early in the night. Don’t wait until the last second and awkwardly fumble through the conversation in front of the waiter or cashier. Offer to pay up front, and if your date would rather pay or split, let it slide without a scene. You will have plenty of opportunities to cover the expenses in the future!

4. Have Fun & Be Yourself!
A date is guaranteed to be filled with uncertainty, anxiety, and shyness from both sides. Accept this reality, and then decide to be yourself during the date! Ensure that you are behaving respectfully and remain chivalrous, and then allow your date to get to know the real you as you have fun throughout the date. The worst thing you can do is try to be someone else to impress your date. Honesty and transparency (appropriately!) is a great look on a date.

5. Respect Your Date With A Follow-Up
The long-awaited question is here: How long do I wait to follow up? Traditionally, the man will wait a day or two before reaching out to inquire about a second date. In today’s digital world, a day can seem excruciating - even more so an hour. However, if she is interested in continuing the dating journey with you, she will be ready and waiting for when you reach out! As a rule, don’t reach out too quickly and too often, and don’t leave her waiting.

The same is true if you aren’t interested in continuing. If you decide that you want to end things, the most important thing you can do is be honest about your feelings and let her know your true feelings.

The above guide - while not exhaustive - should you get down the road to successfully navigating the modern dating world! Each individual and date will be unique, so be ready to adapt and pivot as necessary. However, by keeping the foundation of the above guideposts in each dating scenario, you will ensure that each date is fun, memorable, and likely to lead to a second, third, and more dates!