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Confessions & Critiques Of Online Dating Sites By A Serial Dating Mom

June 3, 2016

June 3, 2016



Single Parenting

by Kayde Richardson

Tilted HeartI am 36-year-old professional single. I have a corporate job along with co-owning three businesses. In addition to that, there are two student-athletes in my life that call me mom. With all that, one may ask where do you find time to date? My reply — all the time!!! That’s because I’m known to my friends as a “serial dater.” I earned this title because I’m on many different online dating sites. I am here to share my experiences on each of the sites, giving you my pros and cons of each site along with tips and tricks to help you navigate through the process.

First, let’s start with some facts about online dating: estimates that 40+ million Americans have taken to online dating. Clearly, the stigma is gone and online dating is now more acceptable than it was years ago. I’m pretty sure you know someone who has used online dating or who met a spouse or a mate from an online site. Five percent of Americans who are in a marriage or committed relationship say they meet their significant other online (Pew Research). US Weekly reports that famous celebrities, including Halle Berry, Jennifer Aniston, Mariah Carey, Martha Stewart and Adele, have tried online dating.  I mean if these celebrities found success with online dating, I had no reason to be ashamed. With those facts in hand, along with me having no time to go out meet people the traditional way my quest began.

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The first site I tried was I attempted to search for my Prince (that’s short for Prince Charming) using my mobile device. When you go to the website you are greeted with a picture of a happy couple and the option to see photos of Black singles near you. You enter your zip code and the qualities you’re seeking in a date. You land on another that prompts for your email address and birthday. You’re almost done (at least that’s what the header at the top of the page says). Next, you create a username and password. It takes you to a series of pages to complete your profile where you add photos, a description of yourself, and how you want to be notified of new matches. Once you are finished with all of that, you will find yourself at the site’s payment page. Select a plan to view their matches. Wait! They want me to pay to view singles that I might not have an interest in or may not even be attracted to? No, thanks. I’ll pass. Plans on ranged from $16.75 for one month to $71.70 for six months with an option to pay with a credit card or PayPal. Their fine print states there is a $3.99 processing fee for all new orders and your subscription will automatically renew for the same price and package length unless you cancel via your account settings page. This site also has a mobile app and desktop version.

Five percent of Americans who are in a marriage or committed relationship say they meet their significant other online” — Pew Research.


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OkCupid profile

The next site I tried was OK Cupid. I was told by several male friends that I would meet a wide variety of men and that it was geared toward young professionals. Um, negative! You follow the same process as above except this site is free to view singles. With the free version, you can see mutual likes, review profiles you liked, view recent activity by other members, browse matches, send messages and view a Quickmatch, which is basically speed searching for a date in your PJs.  You have the option to pay $19.99 for one month or $9.99 for six months for upgraded features like the A-List to see who has liked your profile. The upgrades include being able to see who has read your messages, browse without ads, and the ability to store up to 5,000 messages for the basic package. If you want even more perks and benefits you can upgrade to the A-List Premium package at $34.99 for one month or $26.66 for six months. You get all the benefits of the basic but you turn up the heat to be seen by even more attractive matches, your messages will appear at the top of the receiver’s inbox, you will see the answers to everyone’s public answers, and the option to browse invisibly. My experience on this site has been, “Eh.” I have 32 messages and have only communicated with eight people. No dates. I felt there were no real connections between me and any of the guys on this site.  According to OkCupid, 313 people have liked my profile. I completed all of the information and stated what I was looking for in a date but the matches were the opposite of what I said I was looking for. I have noticed on this site there are a lot of twenty-somethings and gentlemen ages 40 and up. I also noticed that this site wasn’t very ethnically diverse. On to the next dating site.


Since Cupid’s arrow missed me, I decided to go fishing on Plenty of Fish, a.k.a. I should have known this was a bad idea, as I am allergic to fish and shellfish. has a mobile app and a desktop version as well. Like OkCupid, it’s free to set up a profile, browse matches, and customize searches. Upgraded members have the ability to find out who wants to meet you, unlock the user’s extended profile, remind you if you previously messaged someone, discover if they read your message, see the date and time someone viewed your profile, and find out when they were last online. To upgrade from the free version, it will cost you anywhere from $38.99 for three months to $89.99 for 12 months. I will say that I have gotten the most amount of dates from this site. I’ve been on for four years with over 100 dates and four courtships. This site has been the most successful for me when it comes to actually meeting men. My most recent experience lasted one month, and we’ll call him “Almost Mr. Perfect.” We started messaging on Super Bowl Sunday and went out that same evening. He was recently divorced and has adult children. He was not looking to have any more children which was a plus for me with so much already on my plate. He also owned his own home and has a great career. He was 10 years my senior and very attractive. I found the most attractive thing about him was his willingness to wait when it came to having sex. I’m practicing celibacy until marriage. I thought to myself, maybe I’ve found the one. It was a whirlwind courtship. Dates every night, flowers sent to my job twice a week, sweet little gifts here and there. He seemed like Mr. Perfect until his arrogance and temper showed themselves.

“Almost Mr. Perfect” became controlling of my time and was intimidated by my independence. He felt that he should be the reason for my happiness. Up until three weeks ago, we were still trying to make it work. At the end of the day, I couldn’t sacrifice who I am as a person to calm someone else’s insecurities. is worth mentioning here. has a great reputation for protecting member privacy. Like the first dating site, it too has a mobile app and a desktop version. has a free version also like the previous site. Unlike the previous sites, sends you five daily matches. You are able to view profiles for free but have to be a paid member to communicate. Prices range from $41.99 for one month to $251.88 for 12 months. offers a free three-day trial as well as a six-month guarantee, so if you don’t find that someone special, they will give you a free six-month membership. claims to be the go-to app for celebrities and, from my experience, is ethnically diverse. There are also a lot of professionals on this site. Another cool feature that sets apart is the Stir events. Stir events are held in various locations throughout the country to help bring singles together. These are normally paid events in addition to the regular monthly membership fee. Past events have included cooking classes, dance lessons, and speed dating. This site also had more fake profiles than any of the other sites. I’ve only met one person on, a doctor. We stopped dating due to distance and scheduling.




Tinder app profile

Let’s talk about sex or the Tinder app that has been dubbed the “hook up app.” Tinder has a mobile app that is linked to your Facebook profile. Tinder recently offered some upgrades which include using pictures from Instagram, connecting your Instagram profile to your Tinder profile, a super “like” feature when liking a profile, the ability to edit the “About you” section (previously it displayed only your profile information from Facebook). Tinder is very different from all of the other sites and apps. The only way to communicate with someone on Tinder is after you mutually have liked each other’s profile. If you like someone’s profile, swipe right. If you don’t like it, then swipe left. It’s a simple as that. Tinder is also location-based: your matching pool will be focused on where you are geographically at the time of swiping, which brings us to the ‘hookup’ nickname. In my experience, the men on Tinder seem to be more forthcoming in what they are looking for. Some profiles will state, “In town for the weekend, looking to have some fun,” or, “I’m married and looking for a partner for my wife and I” and, “I’m only interested in hooking up–not looking for a relationship.” I have been on several dates since Tinder. I will say that after the first date, every person I met on Tinder expected to have sex.



Voted as one of the top five dating sites by, eHarmony is the most recommended and most complete dating site on the web. eHarmony prices range from $59.95 for one month to $238.80 for 24 months. Every so often, they offer free communication weekends. I started my eHarmony journey in 2012 and didn’t get too far, as I never had enough time to complete the lengthy profile. Two weeks ago, I finally got a moment to myself and completed my profile. One bottle of wine and three hours later, my profile was 91 percent complete. eHarmony asks a series of questions ranging from, “What is the most important quality that you are looking for in another person?” to “What is one thing that people don’t notice about you right away that you wish they would?” You then move on to things that you can’t live without, and to questions, such as how your friends would describe you, and if you drink or smoke. You also get to pick your match preferences and how important each one is to you. Then, the fun begins. eHarmony will send you five to six matches per day based on the qualities of the single matches, scientifically based matching, and their personal matchmakers’ recommendations. From there, you have the ability to ask the match five questions (eHarmony provides 20 or so generic questions to choose from). You wait for the match to respond. Next, you compare your “makes and breaks” in a relationship. If you are still wanting more, eHarmony gives you a chance to dig deeper with three more in-depth questions to ask your match. Finally, you have the opportunity to exchange emails and build a personal connection. Since joining eHarmony two weeks ago, I’ve received 29 matches. I have sent 10 people the first five questions and I have completed the process with a cute IT geek-by-day/sexy dominant by night that is looking for a long-term relationship. The only question that remains is, “Will I be his submissive?”

Photo Credits: from Kayde Richardson and the various dating websites.


Single mom & Guest Writer | @KaydeWishes

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