How to Dating Online

How to Dating Online

how to dating online
Online dating can be a great way to meet people.

My name is Tom. I have dated online for almost 20 years. I can honestly say that online dating can be a great way to meet people. I met my current girlfriend of the last 3 years online.

Dating online can also be a great waste of time, and money, and contribute to emotional stress levels.  The results you get all depend on how you go about it.

I will share with you some of what I have learned about online dating, both the good, and the bad.

Hopefully this will keep you from wasting your time and/or money (like I did), and assist you in finding what you are looking for more quickly, and with less resulting stress.

I will tell you about some of the different dating sites, what to put in your profile on the site, including pictures, and why.

I will also tell you what to look for in other people’s profiles, what to say when you contact someone in order to get a response, and how to correspond.

You will learn the best steps to take to ensure you get a date, where to go on your first date, how to proceed if your date goes well, etc. You will also learn how to achieve your objectives with your new relationship, and a lot more.

Now, it’s true that I am a guy, and I am coming from a guy’s perspective. However, there is information for and about the ladies that I believe can also benefit them.

This will also let the ladies know more about the guys, how we think, and why we do the things we do, which I’m sure can also be useful.

Online dating has been called the ‘singles bar of the new millenia’.

I only wish that I had this information when I started out dating online back in the late 90’s.  Although, I think you will discover that it is mostly just common sense.

It is possible to find your soul mate online.

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Dating Sites

how to dating online
Online dating caters to all different types of people and lifestyles

When I first broached the idea of dating online back in the late 90’s, there were only a handful of actual dating sites. I don’t recall if I stumbled upon it while online, or if a friend or coworker first told me about it. What I do remember is that I was hooked immediately.

I had to see how this new phenomenon worked, and if it was for real. Could it be true that I no longer had to summon courage to approach a woman in a bar?

Was it possible that I no longer had to depend on friends or family members to set me up on dates with their friends?

Could I really look at several, if not dozens of different profiles with pictures of different women, and choose the ones that I am most attracted to, lived close by, and had the most in common with before contacting them?

Today, 2018, there are dozens of dating sites. I have not counted them all, but I would guess the number approaches several hundred different sites.

Many of these dating sites are short lived, as the competition for members has steadily increased over the last 10 years of so, and continues to increase as we speak.

There is attrition of the pay sites, and also of the free ones, as many people will let their memberships lapse once they are in a steady relationship.

The good news for many of these sites however is that a lot of people belong to more than one, and some belong to many sites.

There are still a few general dating sites, but most dating sites now are ‘niche’ dating sites. The different dating sites include free sites, pay sites, Christian sites, Jewish sites, adult sites, gay sites, senior sites, ethnic sites, activities sites, sugar daddy/sugar momma sites, hookup sites, speed dating sites, and many more.

Almost any group or desire is covered in the online dating site world. Some sites are free. Some are free for certain periods like 7 days, and then require that you become a paid member to continue.

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Others allow you to stay a member for free but they limit your access, and your ability to communicate with other members.

Most sites will allow you to begin for free, and at least let you look around, and see what the site is about, what the members look like, how much choice and variety there is, and what the site’s special features are.

Even the free sites have upgrades, and most sites provide much more value as an upgraded or paid member.

You can usually obtain a discount on the monthly membership rates by buying an extended membership. These extended memberships are normally for 3,6, and 12 months. The longer the extension you agree to, the lower the monthly rate.

My experience has been that you usually get what you pay for. With the free sites, you have to sift through a lot of sand to get to the gold.

The members of the free sites, generally speaking, are not as sincere as the members of the paid sites.  By sincere I mean that they are looking for a more serious, long term relationship.

The member profiles on the paid sites are also more thorough, and well written than the free sites. The member’s pictures are also better, as there is a feeling of putting your best foot forward there.

The free sites tend to attract everyone, so you find more people that are less successful, and many have different views, and objectives on life than those on the pay sites. This of course is a generalization, but it has been my experience.

The most popular dating sites in 2018 are:

Paid: Match, EHarmony

Free: Plenty of Fish, OkCupid

Religious: Christian Mingle, JDate

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What to put in your Dating Profile

how to dating online
Be sincere and honest when filling out your profile.

Much of this ‘advice’ is applicable to both men and women, but since I am a guy, it is from a  guy’s perspective.

The most important consideration in filling out your dating profile is to be sincere, and honest. You can’t be all things to all people, and remember, you are trying to find someone that you connect with.

For example, if you are a smoker, you probably won’t get along well with a non-smoker.  I won’t date smokers, but I’m sure there are a lot of smokers that wouldn’t date the likes of me because I don’t smoke. And, so be it.

If you are 5 feet 8 inches tall, don’t put in your profile that you are 6 feet tall.  If you are considerably overweight, don’t put that you are of average build, or even a few extra pounds overweight.

The truth will come out when you meet someone, and if you have misrepresented yourself, you will disappoint the person you are meeting.

They may also think that if you lie about your height or weight that you may also lie about other things.  Your odds of getting a second date go way down.

You don’t have to write a novel about yourself, and your likes and dislikes. In fact, I highly recommend that you don’t get too wordy. Just hit the main points, and you can add a little extra.

After all, you want to discover some things about your date when you meet, and have more to talk about.

When I see a profile that goes on and on, it makes me think that this person is self absorbed, and may have a tendency to want to talk your ear off.  People are busy, and they don’t want to spend an hour or two reading someone’s profile. At least I don’t.

Try to use correct grammar, spelling, and punctuation. Now, I realize that not everyone is proficient in this area. Misspelling the occasional word is ok.

Not having perfect grammar, and punctuation is also ok. But, if it is obvious that you slept your way through school, or that you are dumb as a box of rocks, you will also likely struggle to attract prospective mates.

There are spelling checks, and grammar checks online that you can use, if need be. The site is a very good one for this purpose.

If you struggle in this area, it might be a good idea to run your writing through these before you hit the submit button on the dating site.

Try to refrain from using vulgarity. It is also a good idea to keep from being too political, and keep from denegrading certain ethnic groups, and countries.

You may be 100% in the right, and justified in what you say, but also remember that many people could disagree, or take your comments in the wrong light, and that could shrink your pool of possible prospects.

I’m not saying that if it’s important to you that you should not include it. Just saying that you should consider how your remarks will be taken.

Another statement that I come across quite a bit from the ladies that have kids, is “my kids always come first”.  This may be true, and I can respect that.

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However, if you are looking for a relationship, and you immediately make a guy feel that he is going to be relatively unimportant to you, it will lessen the interest that you will generate.

I think most guys understand that your kids always come first, and you would be less of a mom if you didn’t feel that way. However, you would be better off saying something like, my time may be limited because I have younger kids, but I will try my best to make time for a man that I like.


how to dating online
A good, recent picture will get you more responses.

Putting your picture on your profile is an absolute must. Profiles with pictures, even not so great pictures, get tons more responses than those profiles that don’t have a picture.

The types of pictures you put on your profile may be the single most important thing you include on your online dating profile.

Do not put pictures on your profile that are more than 2-3 years old. I have met a few ladies that looked so much older than their pictures, that I didn’t even recognize them when I met them.

Needless to say, I didn’t want to pursue a relationship with them. In this day and age with cell phone cameras, there is no excuse not to have a recent photo of yourself to post.

I also strongly suggest not to post pictures on dating sites that are too revealing. Unless you are posting to a hook up site, I would try to keep it clean, and civilized.

I have spoken to many women that say if they see a picture of a guy with his shirt off on his profile, they won’t communicate with them.  There are exceptions, like if you are at a pool or on the beach, but generally speaking I would error on the conservative side.

The same thing goes for the females. Although it is enticing to look at, too much exposure only makes you look cheap, and desperate.

If you present yourself this way, you will also attract a lower class individual. I like to leave something to the imagination, at least when long term relationships are being considered.

I am more interested in a woman that keeps things respectable, at least until we get to know each other. Don’t get me wrong. I am not the morality police. You can do what you want, of course, but just remember that your actions have consequences.

It is also a good idea from a guy’s perspective, for a woman to have only herself in her main picture. If you want to include your kids, and others in your secondary pictures, I think that is fine.

If your main picture is of you holding a baby, I can tell you that most guys will be turned off, and it will dramatically lower your incoming messages.

We know that you love your children, and family, but remember this is a dating site. We want to learn about, and look at you. We are not concerned about your family and friends right off the bat.

We may like to know how many kids you have, their ages, and whether or not they live with you, but I would low key the pictures of them, at least initially.

If you are not sure if which pictures you should post on your dating site, I suggest you show your pictures to a friend of the opposite sex.

Obviously, you want your best picture to be your main picture. Picking the right one can make all the difference.

Dating sites always show your main picture on the search results. I have seen main pictures that were not good, and secondary pictures that were good.

Let’s be honest, most people want at least some attraction. If you main picture is not your best picture, you could easily lose prospects.

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How to Correspond

how to dating online
Be polite, friendly, and respectful with your correspondence.

On the online dating sites today, there is often competition. So many people are using online dating that in order to be successful, you have do things correctly. This can mean that you have to stand out.

Assuming that you have a good, readable profile with good, recent pictures, it is time to search for your possible dates.

Most sites will allow you to input the exact criteria of the type of person you are looking for in the search page.  If you get too specific in your search, you will decrease the results.

Determine what you must have in a potential mate, and leave neutral those attributes that you can live without. Once you have found a few good matches, it’s time to start communicating.

The first email that you send is very important. The feedback that I have from the gals is they want guys to write more than a few words.

They want to know that you read their profile, and that there is something in there that has piqued your interest. You don’t have to write much, but what works for me is to be polite, respectful, and to always ask a question about something in the profile.

For instance, if they say they like to play golf, you can ask if they played golf in high school.  Or, if they say they like seafood, you can ask what their favorite seafood restaurant is.  It is a good idea to not get too personal right away, and don’t ask things like, where in town do you live?

Whatever you do, don’t comment on, or ask anything that could be construed as sexual.  This may sound obvious, but I have been told that many guys get very personal right away, and it is a big red flag, and a turn off.

The point is, don’t come off like a creep or a pervert. This will get you nowhere.  Just be nice, act interested, and be patient.

If you come from just trying to make a friend, you will have a better chance of getting a positive, return message.

For the ladies, I think it is ok for you to contact a man on a dating site that you are interested in. It is very flattering for a man to receive a message from an attractive lady.

Normally, you will need to message back and forth at least a few times before you will be able to ask for a meeting. The usual progression is, 3 to 4 emails, then ask for a phone number.

Once you have the phone number, talk on the phone a few times. Then, once you sense that you have a rapport going on, ask for a meeting/date

Some gals don’t need to talk on the phone first, but most do. Being patient is key here.



how to dating online
The best first date is the ‘meet and greet’.

The first date or meeting, I think should be a short one. I have learned over the years that seeing someone in person can be very different from what you expect.

It is better to meet for a drink or a cup of coffee, than to plan on meeting for dinner, and making a night of it. I call this the meet and greet.

You can usually tell fairly quickly, sometimes immediately, if this person is someone that you would like to continue seeing. By arranging for a short first meeting, you can often save each other time and money.

If you do hit it off, and are attracted to your new friend, you can set up a dinner date, or some other longer meet up. I also like to make the first date a walk in a park, or a walk on a high school track.

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It is easy to converse, and you can get a little exercise at the same time. If you hit it off, you can set something up for another time.

If not, nothing lost, and you may have gained a new friend.  Your only loss will be your time at worst.

This strategy will also protect you from what I call the serial dinner daters. These are women that agree to meet for dinner with whomever is willing to take them, and pay for them.

They are often not looking for a relationship, they just like to go out to eat, and they really like that they don’t have to pay.

This brings up another aspect of online dating, and just dating in general. Should the man pay? Should both pay?

Interestingly, this social more was established years ago when the vast majority of women didn’t work and earn money. The man predominantly earned money, so it was required of him to pay whenever he dated a woman.

Today, things are very different. Many women earn more money than men. Sometimes they earn a lot more. My experience though is that many women, despite the fact that they earn as much or more than a man, still expect the man to pay.

My feeling is that all else being equal, this expense should be shared equally. After all, if you expect the same rights and priveledges, you should then also accept the same responsibilities.

I normally end up paying, but I like for my date to at least offer to help to pay once in a while. If they don’t, it will be noted as a negative, and may be cause to stop seeing that person.

At this point I could give advice on how to proceed with the relationship or not proceed. Each person is different. Each situation is different. People have different objectives.

One thing I can say with certainty though is that it is important to be polite, and considerate. If you set something up and you can’t make it, let that person know as soon as possible.

Be nice. The old saying, you will catch more flies with honey than with vinegar really holds true in the dating/relationship world.

If you are friendly, patient, and act like a gentleman ( you know, not a creep ), you will have a much better chance of your new friend sticking around, and it may not be long before your new relationship will escalate.

So, put the cell phone in your pocket, and if you are in a bar, don’t watch the game on tv. Pay attention to your date. I had to learn this the hard way. lol It is also a good idea not to drink too much, at least not for the first few meetings.

I know that first dates can be nerve racking, and I think having an alcoholic drink or two is ok, but I wouldn’t go beyond that. You don’t want your date to think you have a drinking problem, and you don’t want to come on too strong right away, which alcohol can sometimes encourage.

Remember also that many people on these dating sites know each other. If you gain a reputation as a bad egg, it won’t be long before much of the online dating community will find out about it. If that happens, your dating goose could be cooked.


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The Singles Bar of the New Millennia

how to dating online
Online dating makes meeting someone easier than going to bars.

Online dating has been called, ‘the singles bar of the new millenia’.

There are many online dating sites today. There are free sites, and pay sites. You normally get what you pay for. There is every kind of site for almost every person, group, or interest.

Match, Plenty of Fish, and Christian Mingle are the 3 most popular online dating sites as of 2018.

When filling out your dating profile remember to be honest and sincere. Use good grammar, spelling, and punctuation. Don’t be rude or vulgar. Be sure to include a picture in your profile. Upload recent pictures, ideally not more than a year or two old.

Keep it classy. It is easy to take a picture today because most cell phones have cameras. So if you don’t have a recent pic of yourself, take a selfie already.

Ask a friend of the opposite sex to help you pick out your pictures to maximize your opportunities.

When searching for a potential date/mate don’t be too broad, or too specific. Your emails should show that you read the person’s profile, and look for common interests that you can ask or comment about.  Try to write more than a few words.

Be respectful, and patient, but show your interest by attempting to communicate by phone, and then in person. Keep the first date/meeting short.

A meet and greet is often enough to know if you would like to continue seeing the person.

A longer date may then be in the offing. How you proceed from here is strictly up to you.

You will catch more flies with honey than with vinegar, however, if you catch my drift. Best of luck in your online dating endeavors.

Please leave any questions, or comments below. I will be sure to respond directly.  Also, feel free to like and share on your favorite social media.

To your health, Tom

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4 thoughts on “How to Dating Online”

  1. Tom, I enjoyed reading your online dating article. I know nothing about online dating but have friends who met online, even on a dating site and they are perfectly and happily now and for many years. You have offered some very nice advice and some great points to be cognizant of when using an online dating service. Thank you for this information – shirley

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