Dating Expert Tackles Free Online Dating

My goal is to attempt online dating without spending any money or using a credit card. These are my experiences, thoughts, and the lessons that I’ve learned along the way.

Goodbye Ok Cupid

My first day of recording my experiences begins by giving Ok Cupid the finger. Yes. It’s free. Yes there are lots of people on it. And yes, it appears to match you with people you are supposed to be compatible with.

Right now I have 335 people that like me. There are 57 people that like me that I like back that I have never exchanged a message with.

Approximately 40 guys that I have sent or received messages to or engaged in conversation.

So far, all of this has culminated in one real life meeting (far from a date, there is no date before 7 am), a lot of ghosting, and me scratching my head wondering what I am saying wrong.

Well you know what guys, maybe it is you. All of you. Or maybe it is Ok Cupid and the endless stream of likes and messages. Maybe it’s me.

Regardless, this doesn’t seem to be working. Ok Cupid, I think it’s time we start seeing other dating apps. Don’t forget me though, because I’ll probably be back Saturday night after a few too many drinks.


Before I gave up on Ok Cupid, I gave a few people my number. One of them is still talking to me days later. Could he be the one? Maybe Ok Cupid isn’t all bad after all.

After several days of talking, we have tentative plans to meet tomorrow. Could he be the one that I’m looking for?

Update 2:

We were supposed to meet, then he ghosted me. This isn’t necessarily a reflection on the site, however.

Ok Cupid Final Thoughts:

The biggest issue I have found with Ok Cupid is the sheer number of people you can interact with, and being encouraged to keep swiping.

The main method of communication is matching with people and then being able to talk with them. If you have a free account (most people do) this is the only way to message someone.

This means that you’ll have to keep swiping to see who has liked and messaged you.

In terms of chatting and potentially getting to know people, Ok Cupid is by far the best.

What Happens On Happn?

Moving on from my Ok Cupid disaster with my heart a little more jaded than it was before, I decide to try Happn.

The idea of flirting with people that I have actually crossed paths with is romantic. What could go wrong?

Not off to the best start. Happn takes your profile photo from your Facebook account. Of course, it chose a photo of me with my soon to be ex husband.

After some searching through photos, I finally found a few that I felt were suitable if not particularly flattering.

If you’ve never used Happn, it works in one of two ways. It will show you people who you cross paths with, and you can choose to like or pass, similar to Tinder.

If you like each other, it’s a crush, and you can chat. You can also send a hello, which allows you to send someone a message requesting to chat.

Happn: A Few Days In


So I let Happn do its thing and check in occasionally. It feels like a slower pace than Ok Cupid. I am not overwhelmed with messages, and I don’t feel the need for endless swiping.

It feels a little more like dating is supposed to feel. Lighthearted with an element of chance (or fate maybe) thrown in. Perfect for a closet hopeless romantic.

I swipe maybe 10-15 profiles when I check in today. A huge change from Ok Cupid, where I felt like my hands would get tired long before I found someone special.

In general the men I match with seem more inclined to chat. I suppose it’s for the same reason. You aren’t presented with an endless parade of people to like, so (hopefully) you spend a little time getting to know the people you match with.

Profiles are relatively short. Some give very little information, while some are clear about what they want.

Happn A Week In

Not much has happened on Happn. I have met one person that I am still talking to. I have chatted with a few other people, but not very much. I haven’t received a message on there at all in a few days.

Happn Final Thoughts:

Happn moves at a much slower pace than Ok Cupid. There is less interaction, which isn’t always a bad thing.

Happn is good if you have a problem with always searching for the next thing, or if you are easily overwhelmed.

It requires more patience, but it is well worth it if it results in a meaningful relationship.

Happn has been a bit more effective than CMB. I believe it’s a good option for a secondary dating site, especially if you live in a more urban area.


Fetlife is a bdsm social networking site. Essentially it’s Facebook for kinksters. It’s considered proper to proclaim your love for bondage, spanking, and whatever else you are into on your profile.

Everyone Is Should Be as Kinky As Me

You would think a common interest in something like BDSM would help my chances of finding a compatible date. Unfortunately, I have been on Fetlife for a month now as well.

I went on my first “date” yesterday. Met someone for Fetlife for drinks after talking off and on for several weeks.

What could go wrong? 

He was quiet. I was nervous. We talked. Some. The silences were slightly awkward. After two beers for me (and two glasses of water for him, and yes I am rolling my eyes right now), he decided that going home and taking a nap was preferable to spending more time with me.

He did text me later to make sure I made it home ok, but there will clearly not be a date #2.

Fetlife Final Thoughts:

Most of the people on Fetlife seem to be looking for sex and nothing more. It can be a bit difficult to find people on Fetlife as well.

The best way to do so is to join groups and make a post about what you are looking for. Be sure to read the group rules, first. Some of them have specific things that are and aren’t allowed.

I log in occasionally to see if I’ve gotten any messages. I am not very active on there at the moment, so I am essentially leaving it to chance. If someone happens to find my profile and is interested, they can send me a message.

Questioning My Sanity

After all the messages, the requests for sex, and the few guys that seemed more interested in finding someone to marry instead of someone to date, I can’t help but wonder.

Is it me? Or is this dating these days? 

What happened to the days when a man would buy a woman dinner before he propositioned her for sex? What happened to wanting to get to know someone before you decided you wanted to do dirty things with them? Does that happen anymore?

What Is a Girl to Do?

I don’t want a fling. I don’t want to have sex with someone that won’t remember my name in the morning, and I don’t want someone who will pressure me for commitment before the first date either.

You would think that a pretty girl in the city would have no problem finding a date, but I have had a horrible time with it. One awkward date out of a month of online dating.

The truth is that I might just give up, and resign myself to dying alone as the dog lady. However, I have friends that won’t let me give up.

So I keep trying.

Still, a girl has needs. What do I do while I am searching? I buy a few toys and practice some self love. I recommend anyone who is online dating, especially struggling with online dating, learn to take care of their own needs.

I know what I want, and I don’t feel the need to rush or settle for less because I am relatively happy and satisfied on my own.

MetalHead Dating

I love music in general, and heavy metal is one of my favorite genres. Why not find another metal head looking for someone to spend hours in bed with discussing the new Corey Taylor album?

I create a profile only to find that like most dating sites, some features (like instant messaging) require a premium subscription I have no plans of purchasing.

It gets more disappointing when I attempt to add a description to my profile. It says it violates the TOS, even though nothing in it does. I give up and close out metal head dating.

It’s full of ads and not a high enough quality site to be worth paying for, in addition to my technical issues.

Metalhead Dating Final Thoughts:

Given the small userbase and the lackluster site design, Metalhead Dating is simply not worth paying for a premium membership. It is also useless without a premium membership.

The idea of dating based on musical preferences is appealing, so I decided to try

The site is supposed to match you with other users based on your musical preferences, and acts as a place to make new friends and find dates.

It’s a bit overwhelming. You are shown a homepage with lots of profiles in categories including Online, Popular Users, Music Matches, and fans of (an artist that you like).

You can send songs and comment on other’s profiles for free. However, private messaging requires an upgraded account.

It is much less expensive than most premium dating sites, ranging from $10 a month to $5 a month with a 6 month membership, which gives you 6 months for the price you pay for one month on sites like Match.

I have noticed that Tastebuds tends to show you lots of users from other locations, not just your local area. At this point I am not sure if it’s worth paying for due to that and not knowing how many members are actually in my area.

You can search for other members, although it’s difficult to know how active people are here. There’s also soapbox, which is essentially a chat forum.

My profile is created. I added musical artists I like. Wrote an About Me. Time to leave it alone for a bit and see what happens.

I check back into Tastebuds the next day. It seems that you can’t really use the site without an upgraded membership.

A few guys have liked my photos, and one person sent me a song. Which I liked. I was about to give up on the site, deciding it was essentially useless without a premium membership.

Then I realized that you can message someone if you like each other’s profile. None of the guys that liked my photos are local, however, so it is still most likely a waste of time.

As a last ditch effort, I decided to play Get Lucky. This is essentially the site’s version of hot or not. It shows me local people that I have the option to like, but their last online status is usually over a month ago. Final Thoughts:

Tastebuds has a great concept. Unfortunately, the great concept does not translate to a great execution. Save yourself some time and skip this one.

Coffee Meets Bagel

I’ve heard about CMB. I’ve written about it. I’ve recommended it time and time again. Now I’m not sure why it took so long for it to occur to me that maybe I should actually use it.

The easiest way to join CMB is to connect it to your Facebook, so I do so. I spend a little time adding photos and answering the few profile questions.

There are only three profile questions and preferences for your matches are limited to age, distance, ethnicity, and religion.

I realize how accustomed I am to instant gratification to a degree when I finish creating my profile and see a timer with approximately 16 hours left, which is the amount of time till noon the next day.

I can’t see any profiles until then apparently, because this is when they give you your potential matches for the day. I find myself curious about what tomorrow will bring, and a little impatient that I can’t instantly begin browsing at the same time.

Coffee Meets Bagel Day 2

I open Coffee Meets Bagel and check out my matches. Most are reasonably attractive with nice witty profiles. I don’t feel overwhelmed. I do feel a little tempted to go to Ok Cupid to swipe, and realize that I may have a bit of an addiction to it.

It feels much like shoe shopping and needing to try on every pair before realizing that you were always going to buy the first pair you tried on.

CMB seems to understand this as well. I can browse Discover and unlock more bagels (potential matches) for beans (in-app currency). The app gives you some beans for signing up, so you could use this feature a few times for free.

You are asked to add three Ice breaker statements or questions to your profile. These are then sent to your matches, or one of yours is sent to theirs.

This can be helpful for starting conversations, at least I think it could. I got a question about a news article and “ask me about it” with my matches, so it didn’t prove particularly useful today.

CMB Day 3

CMB does a good job of choosing matches. I liked four out of five of my matches, and am genuinely interested in learning more about them. This is a huge change from the endless swiping of Ok Cupid.

Member activity seems to be lower, however. I have gotten a few likes, but I  haven’t had a single chat since I joined.

A few more days in, I have chatted a bit with one person on CMB. At this point I am considering deleting the app because it doesn’t seem to be very effective for me.

Final Thoughts:

If you want to take things very slowly, CMB might be a good option. If you don’t I would suggest using it as a secondary site, not your main focus. There do seem to be quality people on the site. However, they are not very active.

Lessons Learned

I have learned a lot so far from online dating. Maybe I can save you some time and trouble by taking a cue from the lessons I have learned through experience.

Know What You Want

First, I learned what I really want. When I first started online dating, I really wasn’t sure what I wanted. No, to put it more accurately, I had absolutely no clue.

One day I was sure I wanted a relationship, the next day I wanted nothing more than some good sex. In fact, it took having someone almost meet me for sex to realize that I wanted more than that.

So time and a little trial and error, and almost getting what I thought I wanted, helped me figure out what I wanted. Even though it seems finding it may be difficult, I am glad that I know what I am looking for.

Never Apologize For Who You Are

Be who you are and be up front about it. Don’t be shy. Don’t waste time not wanting something that could make someone decide they aren’t interested.

Lay it all on the line early on in your communication. There is no point in talking to someone for a few weeks or going on a date with them only to find something about you is a deal breaker or vice versa.

Don’t seem embarrassed or uncomfortable with who you are either. Present yourself respectfully, but without apology. This is me. If you like it, great. If you don’t, that’s ok as well.

Be Clear in Your Profile

Fill out your profile. In most cases, the more complete it is, the better. Be honest and direct about what you are looking for and what you want.

You do want to leave a little mystery. Don’t put your entire life story in your profile. But feel free to include enough that people have a good idea if they will be a good fit for you before they waste time messaging you.

Keep It Positive

A lighthearted approach is necessary for online dating. If you take yourself or anyone else too seriously, you will quickly end up frustrated.

Laugh at the bad pickup lines and the bad dates. Remember that this process should be fun. Don’t get so caught up in the end goal that you don’t enjoy getting to know people.

Don’t be Afraid to Make Changes

If things aren’t going well, don’t be afraid to change it up. Tweak your profile. Try a different site. Ask your friends what they think you should do differently. They are usually better at recognizing your mistakes than you are.

Put Yourself Out There

Take an active approach. Don’t be afraid to send someone a message. If the conversation is going well, don’t hesitate to suggest taking the conversation to text or a messaging app like Whatsapp or Kik.

The Real Problem With Online Dating

It should be clear at this point that online dating has not gone so well for me so far. I spent some time thinking about what the real problem was.

Was it me? Was it the dating sites? Was it the caliber of men I was meeting? Or was there another factor that is a roadblock to making meaningful connections?

The Connection Conundrum

We are told in our society that more is always better and less is never enough. Hell, more is never enough. We walk around with a sense of entitlement to the best, and would never dream of settling for less than everything.

To an extent, this is reasonable. I would never suggest settling for anything less than what you truly want.

When it comes to online dating, however, it creates a problem. This search for perfection with an endless amount of options creates a real problem.

No one really gets a chance.

We match. We chat. We keep swiping. It seems nearly impossible to strike a balance  that allows you to keep your options open while actually giving things a chance.

Right now I have a list of “maybes”. Haven’t made a real connection with any of them. How long will they stay in the maybe pile? Could one of them be “the one” if I took the time and effort to actually get to know them?

What are we all Afraid of?

What are we afraid of, really? That is what it comes down to. We are afraid to put ourselves out there enough to truly get to know someone. We are afraid of being rejected. Made to look or feel foolish.

At the same time we are afraid of being alone. Deep down we all have a desire and a need for connection. We all want to be loved. Wanted. Needed.

We are also afraid of being disappointed and missing out on our best opportunity for love.

These fears combined with the ease of meeting people through online dating keep us in a conundrum. We swipe. We like. We chat.

Oftentimes, we move on to the next match without ever knowing if that person could have been the one.

We don’t give them the opportunity to be the one. 

There are too many other options, and the risk of slowing down and really getting to know someone seems too high. So we keep swiping, all the while complaining about the process and how we will never find love.

There has to be a better way.

Solving the Problem

Solving the problem takes a few steps and setting rules for yourself. These rules are intended to make your online dating experience effective, particularly if you are searching for love or a meaningful connection.

Narrow It Down

Fomo encourages us to match and talk to as many people as possible. Of course, this means that you don’t really get to know anyone.

Online Dating Rules

  1. Talk to 3-6 people
  2. Limit your swiping
  3. Get past small talk
  4. 1-2 dates per week

The best solution to this is to limit the amount of people that you are talking to at any one time. 3-6 people gives you an opportunity to actually get to know the people you are talking to.

It’s also enough people so when someone doesn’t work out, you don’t feel like you’ve wasted the last few weeks not getting to know anyone else.

How To Narrow It Down

Limiting your potential dates makes sense, but how do you narrow down your list to just a few people?


Don’t be too picky about matching with people. You never know if they will like you back, so move quickly through that part of the process.

Once you are matched with someone, the next step is to see if they actually want to chat with you. Take a quick look at their profile. If you feel like they would be a good match, send them an opening message.

If they reply, then it’s time to take a closer look at their profile.

Must Haves and Deal Breakers

You’ll need a list of must haves and deal breakers. If you are only interested in long term dating, get rid of the ones that don’t have that as an option.

If you are completely monogamous, don’t waste time on someone who is completely monogamy. If you can’t won’t date someone that smokes or drinks, eliminate them from your list.

Isn’t This Backwards?

I know, this process seems backwards. Why wait until someone responds to your message to really consider if you are compatible or not?

Because, particularly for men, but to a large extent for women as well, most of your swipes won’t result in matches. If they do, most of these won’t result in conversations.

So it’s best to run the numbers at first and move through profiles quickly until you see if they are actually willing to chat with you.

If you are using a traditional dating site that doesn’t have swiping as it’s main means of matching, browse profiles and send lots of opening messages.


Perhaps you already have a list of people your attempting to chat with, or are wondering how to narrow down the list of people who have replied that you feel you would be compatible with.

First, you’ll need to create a list of must have’s and deal breakers (see above) and check the profiles for those if you haven’t already.

Next, add wants and dislikes to your list. These are things that you would prefer in a match and things that you would prefer not to have in one. See which profiles match up with this list the best.

If you need to narrow it down further, exchange a few messages (if you just started chatting), or read through your conversations (if you have been chatting for a bit).

Keep going until you have a list of 3-6 people you feel would be a good fit. If you discover someone doesn’t fit on your list, feel free to mark them off and add someone else.

Limit Swiping or Searching

Once you have your initial list, you’ll still want to do a little swiping or searching. This allows you to keep a few people on your list when you decide someone isn’t a good match, gives you other people you can add to your list.

I suggest setting a time limit of 15-30 minutes per day of searching for new partners and composing opening messages. The rest of your time should be spent getting to know the people on your list.

I recommend only sending opening messages or answering an opening message from a match when you have a blank space or two on your list. Once you have actually communicated (sent them a message), not chatting for days or weeks can seem very rude.

Get Past the Small Talk

Small talk to an extent is an important part of getting to know someone. However, when it comes to online dating it can be difficult to move past it and actually get to know someone.

It’s important to ask questions that give you insight into someone’s personality, and to have meaningful conversations. That is how connections begin to form.

200 Questions to Ask

You can find an extensive list of questions from trivial to highly personal with the button above. You can (and should) come up with some questions of your own as well.

Remember that you should keep things fun and interesting. This isn’t a job interview process, and it shouldn’t feel like one. The goal is to facilitate meaningful conversation. To gain insight into someone’s personality, not just answers to questions.

Fun Getting to Know You Questions

  • If you could turn into any animal – which one and why?
  • What would the polar opposite of you be like?
  • If you could transmit any message to literally every person on Earth – what would you say?
  • If you could erase one character trait forever – which one and why?
  • If superpowers got distributed by which one the person needs the most – which one would you get?

1-2 Dates Per Week

Online dating isn’t much good without it’s counterpart, actually going on dates. Actual dates allow you to get a much better feel for who someone is and whether the two of you have any chemistry together.

Just like with messaging, it can be difficult to strike a balance between too many dates and too few. One to two dates a week allows you to meet people and see if you have a connection, without being difficult to maintain.

We all have limited amounts of free time and money, both of which are necessary to go on dates.

Limiting yourself to one to two dates a week also forces you to choose who you go out with carefully.

The flip side of too many dates is, of course, too few. This can happen because you aren’t really comfortable with dating, are really busy, or are shy about asking for dates.

Setting the goal of at least one date every week can give you a little push to get off your phone and go on an actual date.

Final Thoughts

Online dating is tougher than it looks. Ghosting seems to be the norm, sex is considered a reasonable substitute for an actual date, and the sheer volume of people is overwhelming.

That being said I have had some nice conversations, and I still have hope that someday I will find what I’m looking for.

Eventually I will find my happy ending, and it will be worth all the craziness I went through to get there. My advice to you is to learn from my lessons and hopefully save yourself some time and trouble.

What is the best piece of advice you’ve ever gotten in regards to online dating? Let us know in the comments!

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