Things I Learned the Hard Way in the Dating World

I was pretty late to the game of dating so I didn’t know a lot of things.  With every lesson, however, I learned not to make the same mistake again. Some of these lessons were really hard and hurtful to learn but sometimes that’s just the way life is.  I will share the main ones that I learned.

Ask DIRECT Questions

When I say this, I mean you ask you have to seriously ask real questions.  Don’t gloss over them.  Also, ask them in a different way.  Men are funny (I’m speaking on the men because that’s who I dated).  You literally have to pose every single scenario to get them to tell the truth because many will find a loophole so that they are not seen as lying.

The loser that I lost my virginity to was separated.  I had no clue.  Why did I have no clue?  Because he brought me around his family and they welcome me, I hung out at his place, and he had said “No” when I asked him if he was married.  Now, to me, if you’re separated you’re still married. I don’t care what anyone says. So for me to lose my virginity to this jerk really sucked.

How I Learned

When I found out that he was separated, his response to me was “You didn’t ask me if I was separated.” My bad. So asking you if you were married was not the same as asking if you were separated.  NOTED!  I never made that mistake again.  NOW I ask all the questions and I don’t care if someone has a problem with being “interviewed” or not.  You’re not going to find some loophole and then act like you were honest all along. I’m also not going to ask questions that I don’t want to know the answer to.

What I Learned

Family can be just as shady as the dude you’re dating. They will hide skeletons for their family because I guess family is over everything.  You can meet their mom and all that and they won’t utter a sound about a man being married, separated, a deadbeat or anything.  Maybe they don’t care but I care.  And I wouldn’t allow some random to come around my family until I was done with the marriage.  I also wouldn’t allow any of my family to bring people around when they have a whole wife or husband.  That’s just rude but everyone isn’t raised like me.

Everyone’s Definition of Dating is Different

To me, dating is spending time with a person that you are interested in.  To others, it’s hanging out with PEOPLE that you MIGHT be interested in.  Because I am a single mom and don’t have a lot of time to devote to other people, I don’t go out on a lot of dates.  I’m one of those people that will talk to you for months before actually going out with you.  Going out means that I am interested because I actually got dressed and left my house to see you and spend time with you. I don’t just do that and I am not a free meal chaser so I’m not just hanging out with you for free food.  Some women do that but that’s not how I roll.

As a single mom, I have to find someone to watch my daughter, THEN I have to look nice and leave the comfort of my home?  You have to be VERY special for me to want to do that which is why I have been on ONE date last year and I’m fine with it.  It would have been two dates with the same person but he knows the story and we still laugh about it.  I’m sure I will see him again but, so far, he’s the only person I would spend my time with.

How I Learned

This was a very hard lesson to learn and it hurt me because I actually was in love with this man.  I literally spent time with a guy, brought my child around him, spent weekends with my child with him, cooked together, laid together, played video games together, etc and this man told me that what we were doing wasn’t dating.  THAT was a VERY hard lesson to learn.  I thought we were in a relationship.  But his definition of dating and relationships was different than mine.  I was there for him through everything.  His friends even called me and told me that I was good for him and that I should never give up on him and all that. I was his confidant, I encouraged him to take better care of himself mentally and physically.  All that energy and I was just some broad that he was dealing with.

However, once I got tired of being treated the way I was and after he put all that out there (it wasn’t like he was trying to curb me or anything, we literally talked all day every day, and spent tons of time together, he was playing a role and I thought we were on the same page), he then tried to dangle a ring in my face talking about some “I was ready to marry you.”  How can you be ready to marry someone you weren’t even dating?  I’m confused.

WHAT I Learned

That if the words are not said that you are exclusive and are in a relationship, don’t give them relationship privileges.  I gave that man three years of my life on and off.  I supported him through some seriously tough times.  I invested myself in him. I brought my child around him.  She loved that man but yeah, it wasn’t a relationship and we weren’t dating even though me leaving made him say that he was ready to marry me.  I could actually write a whole blog about that ONE relationship and it would be extremely long.  I think he broke me in a lot of ways.

Dating for Sport


I was always raised to date with marriage in mind or to date with a purpose.  It seems that people just date for fun now.  It’s fun.  It’s a competition.  It reminds me of America’s Top Model when the dudes that these women are competing for aren’t even all that great.

This actually goes back to the first point I made about DIRECT questions.  Ask them if they are dating other people.  If I am entertaining anyone, it’s one person.  A lot of people claim that this is putting all my eggs in one basket and I’m fine with that.  Once I find out that he’s not really into me or interested, I can move on with my life.  But I don’t have that great of a memory to date a bunch of people.  I also don’t think you can really get to know ONE person when you’re dating a bunch of people.

I promptly ask if they are dating other people because, honestly, I’m fine with stepping out of the way so that they can find their true love.  I don’t want to jump into a competition.  A bunch of people don’t compete for my time (unless you count my daughter and animals) so I wouldn’t do that to someone else because I would NEVER be available otherwise.

However, I am now cognizant of the fact that a man can give you a TON of his time and still be dating other people.  Technically the aforementioned points tie in to this one.  The story about the one guy I fell in love with is definitely proof of this as well.  I guess he just had a LOT of time on his hands.

Maybe I was dumb because he would try to tell me to date other people which was off when I really just wanted to spend my time with him (and directly told him this).  I wasn’t good enough for him in some way I guess so I had to come to grips with that. It really hurt but I needed to learn that lesson.

It’s really funny to me how men complain about how much dating costs BUT wouldn’t you save money if you slowed down on dating a bunch of people and did sensible things on dates instead of putting on a show by trying to take women to these expensive restaurants just to stomp on her heart later (okay, that sounds bitter but I mean, really).

Meeting Family Means NOTHING!!!!

Some people just bring all the women around their family. Maybe their families are like the judges in America’s Next Top Girlfriend.  Who knows?  I’ve met a number of moms and families.  I guess that’s the new rule: bring everyone around your family and make the woman think it’s something that it’s not.  The loser I lost my virginity to and the guy that strung me along for 3 years both introduced me to their families and close friends.  It’s no longer reserved for people that you are serious about.

Times have changed and actions no longer speak louder than words.  People lie with their words and their actions and it’s just really too hard to tell at this point to take anyone seriously.

People Don’t Like Answering Questions

Because of that experience where someone decided that they didn’t lie because they didn’t tell the whole truth, I have learned to ask more and BETTER questions.  Some men get turned off by this and I’m actually fine with it.  When I had a singles group, I asked a bunch of questions before letting people into the group.  I asked the questions because I didn’t want to leave any room for people to lie. Some of the questions were:

  • Are you married?
  • Are you in an exclusive relationship?
  • Does anyone think you are in an exclusive relationship?
  • Is anyone currently pregnant with your child or thinks they’re pregnant with your child?
  • Are you separated?
  • Do you live with your ex wife or separated soon to be ex wife or girlfriend?
  • Can someone of the opposite sex come to your house without there being drama?

Ask them questions because you don’t want them biting you in the butt later because you didn’t know.  Some baby might pop up on you and you’ll be sitting there looking silly while the man you thought you were dating is sitting up on Maury checking for paternity results.

Just Because they Look Good On Paper Doesn’t Mean They are Good People

How I Learned

My daughter’s father.  On paper this guy looked like a good guy.  Raised in a middle class, two parent household.  His parents adopted two children before having him.  He went to Howard and got a degree, he had godchildren that he was very good with, was a former member of the Coast Guard, and was a teacher.  Who knew he would bounce when he knew I was pregnant, skip from state to state to get avoid taking a DNA test, and “lose” a job, steal his mom’s money (she has dementia), and travel the world?

What I Learned

No matter how long or how well you THINK you know a person, there is always more to learn about them. I knew that deadbeat for 8 years prior to doing anything with him. I thought I knew him but I didn’t.  And here I am with a now 13 year old girl that has only seen her “father” about three times in her life.

Abstaining from Sex is Bad

Many of these dudes don’t want you if you’re not giving up anything.  Some might stay around and fake the funk while being with the other women that they are seeing to make it SEEM like they’re going to wait for you because they’re “interested” but they’re not.  Most of them like to play the role.  If you wait long enough, the texts will fade out and they’ll just fade away which is fine.  Making it known up front that you’re not into just having sex with someone you don’t know is enough to make a man run faster than if they were running from the police.  But it’s cool to weed them out.

When I first started dating (when I was 19), men would wait a whole year before they got anything.  I didn’t really know the value of sex and what was tied to it though (I lost my virginity at 20).  However, at my age now, I did learn the difference between f*cking and making love.  I can no longer do the former.  It’s a waste of time and not even worth dealing with the guy to do.  I don’t masturbate either as I feel that it’s just not worth it.  That connection you feel when you’re with someone you actually love is unmatched. It’s just not something that you can play with so I don’t anymore. When I was younger, I had a whole flippin team but that went away the one time I fell in love and I have never gone back.

Okay, I’m Done

Okay, I think I got off topic but you get it.  These are the things I have learned in my short time of dating.  But there is a reason that I don’t date.  I think I am (well I WAS) more serious about it than many other people are.  And it’s hard to find someone with my dating style that takes dating seriously.  At the age of 39, playing games isn’t something that I like to do.  Because I haven’t dated a lot, this is all I have learned for the most part.

Because I am an honest person and have nothing to hide or be ashamed of, I expect people to give me the same courtesy but it doesn’t work that way.  So either you start playing the game like them (and change yourself) or stay who you are, stay single, and be happy (unless you don’t like being single).  The dating stories I hear out here on the streets are not something I want to be a part of and would likely land me on an episode of Snapped.  So I’ll chill in the cut and watch other people fall in love.  I truly love love but I don’t think it’s for me.  And I’m actually fine with that.

What are some lessons that you learned the hard way in the dating world?



Published by tallgirl79

Blogging about life. Well, my life. As a black, bipolar, mom to a teenager with special needs, well, there is always a story to tell. From my aversion to having a man to my weird experiences while trying to avoid people, it's all there. Being me is.... different but it always makes for good blogs.

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