How-to Master the Online Dating Game

The following is an opinion-based article from my personal experiences using dating apps and dating to marry.

Photo by Shirly Niv Marton on Unsplash

Online dating has picked up tremendously over the past 5–7 years, but 2020 was probably its most active year yet. Everyone, all over the world, was stuck inside with nothing to do besides connect with friends and family online and make new friends digitally.

I am a huge advocate for online dating. I met my husband on Tinder in 2017. I strongly believe if it weren’t for Tinder, we would have never met. Granted, we are in the same field, worked about 15 minutes away from each other, and even his younger brother had been dating one of my girlfriend's close cousins for 5 years; the cards still were not in our meeting favor.

I traveled for work about 40–50% of the time. While off the road, I focused on spending time with my grandmother and catching up with my girlfriends. When I went out, I wasn’t concerned with meeting someone. I was in the moment, enjoying myself.

Swiping through dating apps before bed or early in the morning before work was the perfect way to date and get to know people in my area.

I frequented some of the best and worst dating apps out there before meeting my perfect match on Tinder. Here’s what I’ve used:

• Tinder
• eHarmony
• Match.com
• Bumble
• OkCupid
• Black People Meet
• Plenty of Fish
• Hinge

I am sure I am leaving out an app or two. I feel like I tried pretty much everything that was out between 2015–2017 besides farmers only and Christian mingle.

The day my husband and I decided to be exclusive, I got accepted to The League after being on the waitlist for over two months. I never got to check the app out. There was no need or interest.

Outside of my travel schedule challenges, online dating allowed me to:

• Eliminate people who couldn’t carry a conversation or had poor communication. Just because we have our first conversation via online messaging doesn’t mean you get a pass on grammar, spelling, and the ability to keep a conversation going. “Wyd” messages as a first touchpoint never got a response. If you didn’t approach my inbox with class, I never responded to you.
• Get to know the person for who they are first without heavily relying on looks. Of course, I need to be attracted to you, but the finest person in the world will quickly become unattractive to me if they can’t hold a conversation, be somewhat vulnerable, or seem full of themselves. Profile pictures only go so far.
• Make my own first impression without having to waste my time talking to them. Time is energy. And there is nothing worse than knowing you are wasting your time talking to someone you know is not it for you. Most dating apps users love to share their social media profiles, and I would check out their socials before messaging them back. If your Instagram is filled with selfies, duck lips (yes, cisgender men do this too), and flashy-type pictures. You are not the one for me. If he follows nothing but Insta-models and a ton of women, not for me. If his captions are all lines from Drake songs, SIR, YOU ARE NOT FOR ME! Could I have judged someone too fast and missed out on something, maybe, but I wasn’t willing to find out.
• I get to stay in control. When you are messaging back and forth on dating apps, the other person doesn’t have your number, and they shouldn’t have your social media. That way, they are not checking for me when I am not checking for them. People fail to respond to your text (or message) in the social media era but be all up in your IG stories asking you “where you at.” Get off MY LINE! I don’t like that, so unattractive. Keeping the initial conversation on the dating platform until AFTER your first date keeps a clean boundary and gives you an easy out when things go left.

Photo by cottonbro from Pexels

Let’s move on and talk about setting up your dating profile for success.

Regardless of your platform choice to scroll through future suitors, your profile is your first impression. So make it a good one. Here are my “rules” for building a successful dating profile.

The Profile Picture — This is the first picture everyone will see on your profile; make it a good one.

Tips:

• Use a picture that shows at least half of your body, from the waist up.
• Selfies are OK, but save them for the photo gallery, not the main picture.
• No filters, graphics, or words should be anywhere on the picture.
• Do not use a mirror picture.
• Don’t go super professional/corporate.
• This is not the place for your super cute bikini/bathing suit picture; save it for the gallery.
• Make sure it is current. Don’t use pictures from 5 years ago unless you have not changed, which I don’t think most of us can say. We’ve all changed over the past 5 years.
• Smile or smize. Have some sort of facial reaction. This is not the place for an RBF look.
• Do not use a group picture or pictures with another person.
• Choose an image that shows off your personality.

Photo Gallery — This is where you can provide various images, telling a story of who you are and what you like to do.

• Select images that show off your hobbies or talent. Into coffee shops? Post one of you there. Do you like to read? Share a picture of you snuggled up with a book.
• Include a full-body picture. Do not load up your profile with selfies. This will make someone create their own narrative about the rest of you. Love whatever skin you are in. Show up confident and bold. You are beautiful, so show it off!
• Please smile in at least one of your pictures. Smiling isn’t everyone’s thing, but everyone loves a lit-up face. Not every picture has to be the perfect pout or straight face.
• No group pictures. You don’t want someone to see someone else they would rather talk to in the background. So to avoid this, just leave it off altogether. Trust me this happens, a lot.
• Be careful sharing pictures with you and someone of the opposite sex. This could very much well be your childhood friend or cousin, but you don’t want someone to create their own narrative about your situation. Note: Not sure how this applies to dating within your sex or gender identity. It may be irrelevant.
• Share that bathing suit picture! Don’t let society tell you that you can’t use that super cute two-piece in your dating profile, or you will be judged for it. Share it. But make sure there is a variety of clothing options in your images. Every image shouldn’t be a two-piece bathing suit. Show off your wardrobe!
• Share at least five images. Don’t cheat your future bae and only share 2–3 images. Give a little variety.
• Make sure there is an image that can serve as a conversation starter. Travel pictures are a great option or something that would make someone ask, “hey, where were you at in this picture” or “tell me more about this image.”
• Be careful taking pictures in front of your home, street signs, and car. You do not want any identifying information displayed in photos that people can use to find personal information about you. There are still a bunch of unstable people out there.

Bio — This is where the magic begins.

Pictures tell a visual story, but words will leave a lasting impression on the right person. The worst thing you can do is not provide enough information for future suitors.

Certain dating apps limit your bio to 500 characters to introduce yourself. Use them, and use them well. Other websites like Match.com will allow you to write paragraphs about yourself, asking questions to help you complete your profile. No matter the character limit, provide detail.

Your bio should tell a short story about yourself. Think:

• Who you are
• Where you are from if it’s not the same place you currently live
• What you like to do in your spare time/hobbies
• What you are looking for
• And a fun fact if you are up for it

Most people leave out “what you are looking for.” Never do this. Be specific. If you are looking for a serious relationship, say something like “looking for a partner to do life with.” That says exactly what you are looking for without spelling out long-term commitment or marriage. If you just want to hang out and have fun, make sure you say that too, “life is serious enough; let’s just hang out and have some fun.”

People are on dating websites for various reasons. Some use it to find their special person, while others just want to meet new people and hang out. Whatever your reason is, just be upfront with it.

Some dating apps (i.e., Hinge) do not provide an empty box for a bio. Instead, they offer several questions for you to answer that are in place of a bio. Have fun with these questions, but remember how you answer them will help people learn more about you, good or bad.

If I was to write my dating app profile today, this is what I would say — Baltimore city girl living in South Carolina. Avid reader, I love the 90s and am a habitual weekend bruncher. I’ve lived in 6 different states and love to travel. By day I am a D&I consultant. After work, you can find me on my Peloton or curled up watching a good movie. Extra points if you love horror/thriller movies. Looking for someone to do life with, a person who likes to have fun, have deep conversations, and someone to laugh at all my corny jokes. Oh, and if you’re into it, I’m a Capricorn.

I showcased who I am, showed my personality, talked about where I’m from, what I like to do, my professional background, hobbies, and what I am looking for.

The more information you give, the more ways people can find common connections with you. When someone comes across my profile they could ask me numerous questions:

• What’s your favorite artist/song/movie of the 90s?
• What's the last book you read? Or what are you currently reading?
• What was your favorite state you lived in?
• How do you like living in South Carolina?
• Where is your next travel destination?
• What’s the last movie you watched?
• Netflix or Hulu?
• What’s your go-to brunch order? I didn’t give away too much information. I did not tell my life story. I gave just enough to get the conversation going.

If you don’t provide that level of detail in your bio, it might be hard for someone to find common connections with you outside of what is shown in your pictures. So I encourage you to do the same.

Tip: Write your bio somewhere else before putting it into the dating app profile. I recommend the notes app on your phone; that way, you can always edit and update it as needed. Plus it makes it easier to copy and paste it into various websites if you are feeling up for the challenge of being on more than a few websites at a time. This also helps with spelling and grammar. Read and reread your bio again and again before you decide on the final version.

Additional Details

Other websites that require a longer bio will take more effort than the few lines I gave above. I highly recommend you NOT use the same shorten bio on websites that allow longer-form content. You don’t have to write an essay, but you should provide at least 2–3 paragraphs.

Questionnaires — some dating sites will give questionnaires that will help you match with profiles. Be honest. They will ask questions about kids, education, height, weight, profession, if you’re a smoker, religion, etc. Be truthful! If you don’t want to have kids or date someone with kids, select the right box. Don’t think you can convince someone to think the way you do. It will never work.

Social media profiles — I do not recommend you link any social media to your dating profiles. Even if your Instagram is private, it will still pull in your most recent pictures shared. This gives away too much access to people who have not been granted permission to enter your social world, even if your profile is public. You shouldn’t be on dating websites to get followers, and if you are, make sure you scream that at the top of your lungs on your profile with “Follow me @yourIGname.” Also, watch out for people who find you on social media without your permission. I find that unattractive. Are details and images shared on my dating profile not enough?

Ok, now we have our profile set up, let’s talk about messaging inside the platform.

Some apps give the power to the women first (Bumble), while others allow anyone to make the first move.

I don’t believe in the “I’m not going to message them first” rule that some might have. One of my best friends was this person. I took her phone and sent the first message on Tinder to her now-husband, you welcome boo. You do whatever makes you feel comfortable. My only recommendation is if you see something you absolutely like, make that move hunny! MAKE IT!

When it comes to having conversations inside the dating platform, treat it as sending text messages. Don’t ignore your inbox for days, and expect the person to be waiting around for your response. Also, don’t be super short and frank. Elaborate, ask questions, be engaging. Say good morning, for heaven's sake. Just because the message isn’t coming to your phone number doesn’t mean that you can’t treat it as such. The goal is to get to know someone, not treat them like they are bothering you.

Do not give your number to anyone that you have not met. You do not want people to have that much access to you that early on. Yes, you can block them, but your phone number is tied to so much more — Facebook, Instagram, WhatsApp, Twitter, etc. People can look you up on various websites using your phone number, so give it out wisely.

I gave my phone out to my now husband a day or two before our first date, which I had to ask him out on btw. I lucked up because he ended up being the one. But I waited until the last minute, AND he was one of the very few people I gave my number to. Dates proceeding him didn’t get my number until we had our first date. This protected my space and privacy.

Photo by Jessica Lewis on Unsplash

Dating while online dating

Online dating is designed for your to get to know several people at one time. You can date one person at a time, but I recommend you carry multiple conversations at once until that one person enters your universe that you can’t seem to shake. Begin nurturing that connection before deciding to add anyone else to your dating roster.

This is what I have done and what I recommend to people who ask me for dating advice.

Here is the dating schedule I would recommend to folks.

I would have at least 2 dates per week that lasted no more than 90 minutes; 75 minutes was my sweet spot. I reserved all 1st dates for Monday — Thursday either during lunch or immediately after work for happy hour. I did not do dinner dates or go on dates that required me to leave my house after I got home from work. If I did a weekend date, it was early on Saturday mornings around 9a, and usually a coffee date.

My Friday evenings and weekends were reserved for hanging out with my friends, catching up on me-time, and visiting my family. I did not want to waste that valuable time meeting someone for the first time. People spend too much time on dinner dates with people who they know they will never see again. A free meal is not worth it. I can buy my own meal thank you very much.

This might sound a little over the top to you, but you will thank me when you sit down with your date, and after 15 minutes, you know this isn’t it. It’s much easier to escape a drink than to skip out of dinner or some sort of activity.

What is even tougher is keeping the same time commitment when you are with someone you are vibing with. My first date with my husband was an hour and a half, and while I wanted to stay longer, I ended it after we had two drinks and shared an appetizer.

Our next date was lunch during the workweek, and he ended up coming with me to Target afterward. The third date was bowling and then a dive bar after work on a Thursday, our longest date at this point. Our fourth date was on a Saturday morning at 9a for coffee.

We did not have an in-home date until date #5. He invited me over and cooked dinner.

It took us almost 7 weeks to get to date #5 due to our schedules. Since we spent “bite-sized” time together, it made for better phone conversations in between and left us wanting to see each other more.

This “schedule” is not for everyone, but when I’ve recommended it to friends, they appreciated it because it took the pressure off from dating multiple people.

If you went to dinner with everyone on the first date, a lot of time is given to someone you are unsure about. Committing to a drink after work or coffee during the day is a great way to jump right into conversation; no small talk about the menu is needed.

Sometimes you might match with someone and meet them out for a drink the same day. I’ve done this before, and it has never worked out. I have always declined same-day invitations. It gives me a chance to weed them out based on conversation first.

Note: While I was adhering to this schedule, I had a flexible job that allowed me to set my own pace and workday, and I also did not have any children that I needed to arrange childcare for. However, if you are a single parent, lunch/coffee dates while they are in school/daycare are highly recommended.

Let’s talk about discussion topics during your first date

Photo by cottonbro from Pexels

I say your first date depends on the type of situation you are looking for. Everyone is going to do first dates differently. But if you are reading this article, more than likely, you are not looking to date for fun or a quick hookup. You are seeking something with some substance and long term.

If this is the case, I suggest you don’t sugarcoat anything and be upfront and honest with whomever you connect with.

This doesn’t mean you host a TEDtalk that you want to get married and have 5 kids, just make sure your intentions are well known. If your date says certain things that do not align with your relationship goals, make note of that. Follow up and ask why that’s their opinion or why they feel that way. Most people allow people to just respond to questions without following up. Never do this.

There is a way to ask about marriage and kids without directly asking about it or sounding pushy. Here are some good questions:

• When was your last relationship? Why did it end?
• What are you looking for in a partner?
• How has dating been for you?
• Tell me about your family. What are they like?

Their response to these questions almost leads to a marriage and/or kids conversation. It’s a natural progression that doesn’t feel invasive.

I am all about probing questions. I prefer to know what I am getting into upfront versus hanging back in the pocket and letting things come to the surface. Time is priceless, and I refuse to waste it.

I also think it’s important to talk about a person's career and professional goals. Let’s be honest, NO ONE wants a lazy, unmotivated partner. Everyone wants to be with someone who has some sort of drive and aspiration to keep moving forward.

It’s up to you what type of career or profession you are open to accepting from a person. Don’t let someone judge you for having whatever standards you have. HOWEVER, do not demand something of someone you do not have for yourself.

Be open, because you never know what you might come across. I once dated an electrician, and I realized I was very uneducated about trade industry professions. Don’t judge a person by their job title. But have your non-negotiables for professions.

These were mine:

• No nightlife workers (promoters, club DJs, bartenders, bouncers, security, etc.)
• No professional athletes
• No independent fitness trainers
• No vague professions, i.e., you never understand what they do

One might say I am judging, and hey, to each its own. I’ve had multiple experiences with each type of person, and it’s never worked out. So why keep putting my hand in the same fire? It’s only so many times you will say, “this person is going to be different.” No, you need to CHOOSE differently.

Your list might grow as you begin to explore different people and what they do for a living. I’ve heard it's hard work dating a professional chef. I haven’t had that experience, so I couldn’t count that person out until I’ve experienced it.

The conversation about a job should have already happened during your back and forth messaging inside the dating platform, but if it hasn’t, talk about it on your first date.

Finally, you should be talking about how this person fills their free time during the first date.

If you are looking for a serious relationship and commitment, some responses might be red flags.

These were some of my red flags:

• Frequent club or nightlife goer
• Hanging out with lots of friends of the opposite sex (this might not apply to dating within your sex or gender identity)
• Nothing. While I enjoy a good weekend inside, dating someone who never leaves the house is also a no for me.

Then there were the things I were looking for in a response from someone. Like:

• If they like to go to museums or enjoy the arts?
• Do they enjoy reading?
• What type of outdoor activities do they like?

Understand that a person’s hobbies will become your hobbies once it gets serious. If the gym is their hobby, you better be someone who loves going to the gym. If they enjoy hiking, you better get into it.

There are some hobbies that people like to keep to themselves as a sense of release or alone time. You have to be OK with that too.

Say your person loves cars or golf. They might travel to attend car shows or play golf a couple of times a year. You gotta be OK with all of this.

Don’t think you can change someone’s hobbies, and do not change your hobbies for anyone.

If you love social media and document your entire life on IG or TikTok, do not change that for that someone special in your life. They either take it or leave it.

Hobbies are a part of a person, so it’s important to understand how someone fills their spare time.

Dating Etiquette

This section can apply whether you met someone online or in person. A first date sets an impression, and the dates following describe the person's consistency and follow-through.

While it is important to make a good first impression, the dates following are just as important. The way you date someone (or how they date you) tells you more than you think.

Show up on time. We are way past the I’m going to be fashionably 15 minutes late for the first date. Because trust me, there is someone out there that is on time, all the time. Plus, what is that telling your future suitor? That you don’t value their time? You are going to have to wait for me moving forward? I don’t know how to manage my time?

Things come up, work, kids, emergencies. When they do, make sure you immediately let the person know you will be late. And don’t fib saying a few minutes when you know it will be 15-20 minutes.

There is nothing worse than waiting on someone who you don’t even really know. What is the point of that? If your date is at 7p, be there at 7p. Everyone’s time is valuable. Make that person feel like they are a priority in your busy life.

Put your phone away and on silent. Do not use your phone during your first date, even when your date gets up to use the restroom and leaves you at the table. Are you not able to sit with yourself or thoughts for 5 minutes without the distraction of your phone?

If you must check your phone because someone is watching your children, or you are on a lunch break, do a quick skim of your lock screen to see if someone is trying to reach you. Do not open your phone and scroll on social media. All that can wait until you are at home; your date is not the time or place. You don’t want your date to return to the table with your face buried in the phone. Not attractive.

Phone behavior during dates, even when you are in a committed relationship or marriage, should be limited. You are on a date to spend time with each other, not your phone. If you can’t resist the urge to pick up your phone to see what other people are doing versus paying attention to the beautiful soul in front of you, then you might need to reevaluate the person you’ve decided to spend your time with. Why can’t they hold your attention, or why can’t you hold theirs?

Be honest, open, and vulnerable. You should be practicing all three from the moment you create an online dating profile, but it is crucial to be honest and transparent during your first few dates.

Being open does not mean sharing your entire life story night one, but if that is something YOU choose to do, that is OK. Do not let anyone tell you how to communicate or share your story. Only you can determine that. But you do have to share something.

When your date asks you questions about your life or experiences, be honest. You can tell the truth without exposing all of your deepest darkest secrets. There is nothing sexier than a person who is honest with themselves. Do you want to be that type of person?

Never ghost. We are all adults here. Let’s not be childish and block someone or stop responding to their messages and calls without an explanation. That’s not how you handle uncomfortable conversations or people and things that are not for you.

If your first instinct is to block or ghost someone, the real question is why? Why are you unable to communicate to a person who spent their time, energy, and possibly money on you? Why can’t you give them the courtesy of letting them know that this will not work out?

Don’t use the “it’s me, not you” line either. Or the “I’m not looking for anything serious right now” when your profile (or you verbally said) you were looking for a relationship. Be honest and tell the person exactly how you feel, tactfully and respectfully.

The only time ghosting is appropriate is if the person on the date was outright rude, disrespectful, or made you feel uncomfortable. Also, if you get the vibe that neither one of you is feeling each other and neither person reaches out soon after the date, it is OK to let that situation just float away.

Follow up. If you had a great time on the date, let the person know. Don’t sit back and wait for them to reach out to you. Yes, you want someone to pursue you, but that doesn’t mean they have to do all the work. Dating is a mutual act. You have to be dateable. Why would I want to date someone that requires one person to make the first move every single time? Learn to share the role of leading in the dating game from time to time.

You are not the only one. Do not think for one second that you are the only person they are dating and vice versa. This is important to understand because their schedule will depend on their life availability, including their dating schedule and yours.

Expect the person to be chatting with other folks when you enter the picture. Don’t look at it as competition, because YOU are the prize. And if that person can’t see that, then it’s time for you to move on. They will make the space and time for people who are worth altering their schedule for.

How do you become that person? Show up on time to dates. Limit phone use. Follow up. Be confident. Share the dating lead from time to time. Take the initiative. Be open, honest, and vulnerable.

When your suitor is clearing their roster to make room for you, give them time to do that. Like I told you not to ghost others, don’t expect them to do the same thing. Someone with stellar character will have a conversation with people to let them know they are no longer interested or have found a connection they want to explore further.

I asked my husband how much time he needed to clean house, and he told me to give him one week. One week later, it was just the two of us.

Final thoughts

Dating is fun, but dating with a purpose, in the beginning, might feel like a full-time job; because it is. There should be no shortcuts when you are searching for your special person. As much time and effort you put into cultivating your friendships and spending time with family, you should put that and more when selecting your life partner.

Why do people think it’s easy to find someone to spend the rest of their life with? Think about that for a minute.

You have to date to find your life partner. Some people forget that too.

Be excited about the journey. Meeting new people is fun. Don’t approach this journey and process as a daunting task because the person on the other end will feel that energy, which could turn them off. Get excited that with each person and each date, you are one step closer to the one.

Don’t get discouraged. You will meet your person when you are supposed to. Don’t compare another’s journey to love to yours. If you feel like you are running into dud after dud, that is OK; we have all been there before. Keep going.

People sign up for dating apps every single day. Don’t throw in the towel too soon if nothing has transpired after a few weeks. It took me two years of “off and on” usage of Tinder to finally find the right person. Your person is not going to show up overnight, or maybe they could. The point is to be patient and trust the process.

Marriage is not for the weak, and dating with a purpose, to marry, shouldn’t be either. It takes effort and choices every single day to be in a long-term committed relationship or marriage. The same goes for dating.

Know when to compromise. If you are searching for someone to check every single box on your list, good luck. But I can tell you that the perfect person for YOU is out there, and they will leave a few boxes unchecked. That is OK. Understand your non-negotiables upfront and do not budge on those; everything else should be up for discussion.

Be realistic. Don’t expect someone to give you more than what you have to offer. If receiving gifts is your love language, be prepared to shower your partner with tokens of love and appreciation. Nothing in a relationship is one-sided. One person might prefer something more than the other, but that doesn’t mean they don’t want or need it. If you are looking for your partner or spouse to take care of everything, make sure you are upfront with that. Don’t expect someone to foot the bill for every single thing moving forward.

Don’t pretend. Everything you do while dating, you should continue to keep up with throughout your relationship and marriage. Life changes, and things will come up. Comfort levels settle in, and everyone gets lazy at one point, but don’t pretend that you are into something or do something that you know is not sustainable for the foreseeable future.

If you are not a chef at home, don’t pretend to do so. If consistent cleaning isn’t your forte, don’t pretend you deep clean your place every week. Because guess what, your partner is going to think this is how life will be with you. You want to make a great impression, but they need to see you in your brightest moments and the days when you feel like leaving a sink full of dirty dishes or a laundry basket full of clothes, clean or not.

Beware of…

Dates that talk too much about themselves. If your date takes up the airtime without learning or asking anything about you, that is your cue to exit. Airtime should be shared during dates. One person shouldn’t be occupying all the talking time. If you are playing double dutch to get into the conversation, ask yourself, would you be cool with this type of conversation forever?

Nonverbal communication. Most people are concerned with how someone carries on a conversation during a date but don’t forget about another major form of communication, nonverbal. How is your date's eye contact? Do they appear to be looking straight through you or paying attention to exactly what they are saying? What about a wandering eye? Dining etiquette?

No compliments. This might sound a little shallow, but everyone loves a good confidence boost. If your date does not respectfully compliment you, then I say NEXT. You spent time and energy getting ready for this date. The least they can do is compliment you. Make sure you dish out a compliment or two.

Helpful behaviors. Depending on your activity, you might need your date's assistance. How are they assisting or helping you navigate through a large crowd? Do they open doors? Pull out a chair? Walk ahead of you? Stand up to greet you when you first meet them? A great companion will have amazing helpful behaviors no matter their situation or who they are with, date one or date 300.

Who's ready to swipe to find the right one?