How To Turn Online Chats Into Real Life Dates And Romances

online dating

Should I Try Online Dating?

Technology is our friend, and there are those who claim that technology helped a lot in finding them love, relationships, or mere hook-ups. Your phone can be a better wingman, or wing-woman, than any of your friends on a night out in a club when it comes to online dating.

Both men and women appreciate that talking through a dating or chat site makes it much easier to strike up a conversation and overcome their social anxiety.  Their shyness and vulnerability are decreased, and they feel more relaxed during the getting to know stage.

Another win is the fact that you don’t have to spend a dime through online dating. While some have premium service fees, a lot of them are available as free apps and websites. No need to spend on coffee, dinner or movie. Something that discourages some people on dating is the fact that it can get pretty pricey, as per Daily Mail.

The most recognizable pro with online dating – is the convenience, as was discussed in Entrepreneur. In between your school/career/business, family, and friends, finding time just to scout the sea for some fish you like is a futile exercise. But with online dating, you can do it when you have some minutes to spare, on your computer or your smartphone – on the bus, during lunch break, in the bathroom… Just about anywhere your wifi or data can reach.

How to Succeed In Online Dating?

How to Ace Your Personal Branding?

Companies make sure to communicate in their branding who their target audience are and what/who they are. Their advertisement provides the most necessary details without overloading you with information For online dating, your ad/branding is your profile. You must communicate clearly:

Your Username / Display Name

Treat it as if you’re applying for a job, make it professional. Use your real name or real-life nickname. Or use words that would somehow give a good description of what you’re about just by your user name. None of those Magic Stick, Temptress, MyMilkshake, Dig Bick, etc.

Using your real name makes the person at the other end know that you’re an actual person, not some sex-crazed teenager, a bot or a phishing scam waiting to happen.

Basic Details

Like age and location. Make the location not so specific that they can stalk you, but specific enough that they get an idea of where would be a good place to meet up, if you ever decide to.

Age must be provided because the only reason you’d refuse declaring it is that you’re a pedophile trying to lure in potential prey. Age ain’t nothing but a number – but a very important one for filtering matches.

Profile Description

Provide a concise description of who you are, your interests and what you are expecting out of online dating.

It is better to be truthful from the get-go, as potential matches usually read this to see if your expectations are aligned with his/hers. Transparency and honesty work like a charm, as it allows the other individual to see if you have matching interests, values, etc.

Say something about your job (save the nitty gritty when you’re in an actual relationship, or just keep it within your workplace), your hobbies and interests. This allows potential matches to think of activities to share.

Never overload it with an exhaustive list of things that you like, love, hate, and your deal-breakers. This can easily backfire as people might think you’re too high-maintenance. Slowly dish these out during the chatting phase.

A few sentences or bullet points will be able to provide a vivid enough summary about who you are and what you’re about. Maybe include a sage quote if you’re into that. Use it wisely, but remember to keep it friendly.

This Zoosk listicle provides some amazing samples of profile descriptions that work!

Profile photo

Use a photo of you – you only. That hot vocalist from a slightly famous indie band, that’s not you. Neither is Ironman or Wonder Woman.

Use a headshot, your BEST headshot, for your main photo, preferably showing a significant portion of your face. No sunglasses – people want to see the eyes because we get a glimpse of one’s soul through the eyes.



Those adventure shots, travel photos, creative pics and candids… we still want to see those, but you can leave those as supporting photos. Make sure you’re alone in the photo, people can easily assume that you’re your hotter friend or sibling, and that’s just unfair.

Do basic photo enhancement, correct the lighting, crop out unnecessary details, among others But don’t overuse one of those photo-beautifying apps where you’ll end up looking like a no-pore KPop superstar. If anything, that will just cause disappointment in the present and in the future.

Daily Mail gives a comprehensive guide to ace your profile photos in this article.

How To Chat With Your Online Date?

Some people avoid traditional dating because of their fear of approaching a stranger, initiating a conversation and establishing rapport until it develops into a relationship.

Those people are quite in for a treat when they realize that online dating isn’t much different, especially if your goal is to get an actual relationship out of it.

Apart from advertising yourself, and making sure your product (you) reaches your target market, chatting a.k.a. ‘The pitch’ is significantly important in getting buy-in from your prospective clients. If you have a great profile but just fail at conversing, you’re only good on paper, but not much substance in real life.

Hey Saturday provided guidelines on things you should remember when chatting on an online dating site or app, ensuring that you don’t get any of those awkward introductions-only chat threads.

Ask Questions

As with real life dates, make sure you do not hog the conversation by telling so much about yourself. Asking questions allow the other party to tell their stories if they’re not as comfortable to initiate them.

This also lets you get off the hot seat and from a mental diarrhea of random things you want to share. If you want a handy cheat-sheet of questions, Zoosk provides one here.

Flirt Inconspicuously

Unless the only reason you went on an online dating is to get some quick bang, then be a little more tactful about flirting.  Flirting too early in an online dating scenario can be a deal-breaker and turn-off. It usually is the biggest telltale sign if a person is on the online dating platform in just looking for a hook-up.

Someone who is hoping for something more long-term and serious is less likely to flirt early on, and would rather prolong the getting to know phase. Stay on the conservative side if you want to get a meaningful relationship out of online dating.

An easy fix in determining and choosing your words and subtle flirting strategies is by asking yourself:  “Would I say or do this in real life at this point of knowing someone?”.

Keep it Real

Because why the hell not? Pretending to be something you’re not or wanting something you don’t can only get you too far. There are too many books, movies and TV shows made about it. That should’ve been enough to learn a lesson.

By keeping it real, it also goes that you be a decent human being. If you have other motives other than having a relationship, make sure it is expressed and consensual. Using hypnosis or mood-altering substances to feign consent is not consent. None of those money, fraud, phishing scams, human trafficking or date rape modus. If you need financial support, a sugar daddy or sugar mommy, or if you get sexual, keep it consensual for both involved parties.

How to Turn an Online Date to a Real Date?

Sometimes we get wrapped up with our idea of the person that instead of taking it to real life, it stays as an online thing. It is too exciting and fun that we don’t want to kill the fantasy.

Taking an online relationship offline is the normal and natural progression if the reason you signed up for a dating app or site is to have a real relationship. Not an eternally, exclusively online beau that your friends start thinking that s/he is just a figment of your imagination.

While online dating is your foot in the door towards a relationship, it cannot be the by-all and end-all of the relationship. To transition your online chats to real life, here are some baby steps to get you from point A to point B.

Step away from the dating platform and text

This is significant despite minute change which tells the person that you’re willing to have her/him know more about you in real life by having access to your mobile/phone number.

In the platform, you might just know them by their usernames, and you may think s/he could easily be a chatbot of sorts. One can easily stop responding, delete the app, or block you.

With a phone number, you bridge the gap, even if you’re still just texting. The fact that you have a phone number means you’re able to buy a phone sim card, and/or apply for a phone line – which immediately means you’re a legit legal entity existing in the same universe.

Add them on social media

This will provide them a glimpse into your life through your photos, check ins, activities, opinions, and posts. This will allow them to get to know you more deeply and understand you, outside the interests you merely listed on your online dating profile.


The first step to adding IRL elements into your dating app encounters is to hear someone’s voice. This adds a human touch to the relationship without doing a full-jump. Hearing your online beau’s voice provides depth into the relationship.

Intonation, pitch and other elements of the voice can communicate cues and emotions which are significant in establishing compatibility and longevity of relationships.

Video Call

Add more human touch through video call. This allows both to hear each other’s voice and see each other’s expressions and reactions.

This is the closest thing to an actual real life interaction, hang out or date, which lets both parties observe body language and non-verbal cues.

How to Turn Your Online Date to an Offline One?

Proposing to meet-up is the final step from keeping it low-key online to testing if the friendship/companionship/relationship you’ve maintained can make it IRL.

When is the Best Time to Meet Up?

Deepen the interaction and take it to the next level by meeting up. Based on a Telegraph article, a survey was conducted and the results showed that the optimal time to meet up with someone is between the 17th and 23rd day of your online interaction.

Of course, this period will significantly differ depending on the frequency of your online conversation. If chats are frequent and on a regular or daily basis, sticking by the prescribed period will be useful. But if there is an irregularity in the communication or other factors that would just deem it humanly impossible for a meet up to happen, that is completely alright. As in the case of this adorable Tinder match who waited 3 years before they finally meet up because they’re too busy with other life stuff.

The parties’ attitudes towards the meet up is a great indicator of their interest and intention. Meeting too early may suggest ulterior motives of sexual encounters, while meeting too late may denote their level of commitment to the brewing relationship.

How to Ask To Meet Up?

Your Tango suggests evading the word ‘Date’ when you do decide to meet-up. The D-word tend to put unnecessary pressure, making it seem like such a big deal.

Ask him/her to meet up, have lunch, or grab coffee. This makes the event more relaxed and casual, no need to fuss and dress up. The terms have lunch and grab coffee likewise evokes a sense that it will be brief and time-bound. So, none of those after-date shenanigans.

What to Remember Before Meeting Up?

Be on the side of caution, no matter how trustworthy, honest and respectable the person might be online.

Choose a Public Place

First-time meet-ups are recommended to be done in a public place. Stop being a cheapskate by suggesting his or her place. If things go awry, it is easier to leave a restaurant or coffee shop than a person’s apartment. It is also easier to get help even from strangers when you’re surrounded by people.

Let Someone Know

Tell your room mate, colleague, friend or family that you will be meeting with a person you met online. Again, to be on the side of caution, just in case something happens to you, people will have an idea whom you were with, and where to search.

Have a Backup Plan

Tell your date that you have something to do, or somewhere to go to after your date. Mentioning this early on lets you set expectations and allows you to respectfully end the evening if things didn’t end as you would’ve wanted. If you find yourself enjoying the night, you can always say “you’ll skip that thing and just hang out with her/him instead”.

Where to and What to Do on a Meet Up?

The most common first date ideas fall in between fancy fine-dining, or dinner and a movie setting. Meet Mindful, however, advises against these because, on your first meet-up, the last thing you’ll need are pressure to hold a conversation for an hour or two over a proper dinner, or a no-interaction movie date.

According to them, the perfect first meet-up date ideas involves the couple talking to each other spontaneously and doing activities that can bond them but don’t take too long.

Some meet-up ideas that promotes talking and getting to know each other and are fun at the same time

  • Walk in the park or beach – whatever’s in your vicinity
  • Trip to the zoo
  • Amusement park
  • Museum visit
  • Video game arcade
  • Bowling or golf
  • Coffee catch-up
  • Brief lunch-out

Why Online Dating Fail?

Trigger-Happy Swiping or Filtering

Tinder gamified online dating by assigning swipes to whether you like or dislike a person. And it is quite easy to get hooked on auto-swiping on photos as if it is a game of Fruit Ninja.

How many times have you mistakenly swiped left when you should have swiped right and vice-versa? Sometimes our muscle memory messes up and fails us. Before you know it, you’ve filtered out a very attractive girl/guy with the most unassuming, kind smile who seemed to have a fun personality. It is quite ok if you can go back and review your choices, and maybe message someone you might have missed.

Lay off the obsessive trigger-happy swiping and just slow it down. Why are you rushing anyway? Remember the reason why you’re on a dating site or app in the first place. It is to find a suitable match – whether it’s a relationship you’re looking for or a hook-up. You don’t want to end up with a pretty girl who’s got daddy issues, or a hunk of a man meat who’ll scam you. Or completely miss out on a potential soul mate or an amazing one-night stand.

Focusing on Looks

Admit it or not, sometimes we fall prey to superficiality. We swipe left and right based on the primary photo alone. We’re not even bothering to check on 5 more photos of him/her in a more flattering light, in an exciting adventure, let alone make it as far as their profile description.

By focusing solely on their physical attractiveness, we forget the fact that relationships do not exist and survive on just merely being a good-looking couple. Just think about all those Hollywood love stories which just end up in divorce. Keep that in mind when you find yourself ogling on your choices and zeroing in on that girl with the Kardashian looks or the guy with Harry Styles’ style.

Check their secondary photos, that average looking guy or girl might have a photo sky-diving, cuddling with their dog, or cooking. Things that could potentially interest you. Read their profiles, the bimbo-looking girl or the stupid jock guy might be a geek in disguise. Check their interests, like travel, science, culture, philosophy. They could have listed their preferred movies, books, and TV shows – you can’t find that on the photo alone.

Remember, everything is not what it seems, and as cliché as it sounds, don’t be judging books by its cover.


Don’t be the douche or bitch who’ll throw expletives if the other person does not reply within 5 minutes. That other person probably has a life, career, family, friends, and hobbies that keep him/her busy. Not everyone is lurking on a dating app or site 24/7 for a sign of anyone who’ll chat them, and sign off their stories with a happily ever after. Or is interested in hooking up that same night.

Just with anything in life that is worth having, patience is needed. Patience is a virtue, and it has its value. Just look at this couple who practiced lots of patience, courtesy, and humor and are now off to Maui for their date – all expense paid by Tinder.

Chat etiquette

For some reason, dick pics have been chosen by a few of the male population as a pick-up line. Blunt questions that immediately put the conversation in a state of sexual awkwardness also happens.

If you’ve checked his/her photos and his/her profile, you’ll have an approximate idea if dick pics, boob photos or sexual innuendos will work on them. There will be some who’ll be up for it, and that is perfect! But more often, they’ll think of such as improper and rude. You might find your prose and self-portrait viral and public laughingstock instead of finding a potential match.


Self-sabotage can happen in the online dating space when we misrepresent ourselves and our expectations.

Saying that you’re a “fun-loving woman who just wants to have some fun” can be misinterpreted that you are game for hookups. When what you had in mind is you’re not looking for anything serious and want to just date around, no sex involved.

Go through your profile one more time. Or have a friend proof it. Ask them what they think and what your words might mean for other people.

Not Taking It Offline

There is a shelf-life to online dating. Perhaps the biggest contributor to online dating’s ‘failure’ is people’s incapacity to realize when to meet-up and take the relationship to the next level, into the real world. Online dating will lose its spark and novelty, and it is best that before that happens, the parties involved will take the initiative to try something new to reignite the excitement and bring back the sense of newness.

As with any relationship, it takes effort from all involved parties to ensure they keep things exciting so as not to bore each other and extinguish their fire.

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