How To Starting Dating Again

Now that Valentine’s Day, 2011 is over and you just found out that you’re not your significant other‘s primary relationship, you’re probably thinking about bouncing… breaking up with that person.. ending your relationship and starting all over…

We’ve already talked about how to get over your ex-boyfriend and how to get over your ex-girlfriend, but those are emotional considerations.

Getting back in the game might be a bigger leap than you imagined, so let’s discuss a few issues…

Hooking Up

There are lots of benefits to having one boyfriend or girlfriend. One of them is that you definitely know where your sex is coming from (Though, I know quite a few women that would beg to differ with that remark).

You know what it’s going to be like. You know how good or bad it’s going to be. You know what physical shape your SO is in. You know what they like. You know what they do to you. You know how they respond when you do things to them. You know whether they run their mouths incessantly, like they think they’re in a softcore porno or whether they STFU. You know whether them move a lot or lay there like the proverbial dead fish. You know what their fetishes are. You know what their safewords are…

Once you exit that relationship, all bets are off. You could meet the FOYINEST chick in history and she could turn out to be the wackest lay ever. 🙁 Look how Prince had to kick Kim Kardashian off the stage! 😀 haha You can have all the ass you want, but if you’re not gonna DO anything with it, get the **** off the stage! 😀


Even though your SO might not be the sharpest pencil in the box, you’re pretty used to them right now. Their weirdness is predictable.

When you start dating again, you’re exposing yourself to people of questionable mental condition. You never know how much baggage they’re bringing to this relationship from the ones they’ve had before. You never know how much trauma they’re still carrying around from their upbringing, either at home, or because they didn’t have good relationships and friendships while they were in school growing up.

The things you detest right now about your SO might be a walk in the park, compared to the new people you meet.

Unfortunately, most people’s styles of dating involve hiding their eccentric qualities until AFTER you get involved with them, so it’s going to be quite a while before you find out who you’re ACTUALLY dating.

False Advertising

It’s come to my attention recently that there’s a massive amount of false advertising that goes on when it comes to online dating.

I talked about this a couple of years ago, in “It’s All In The Game (Online Dating)”, but I’m now aware that the situation is worse than I thought.

In that post, I was responding to a gal who had said that guys were claiming they were 6 feet tall in their dating profiles, and then when she met them, they weren’t anywhere near that height. I explained to her that it’s all in the game.. If they don’t say they’re tall, she might not go out with them at all. If they lie about it, they still get a chance to try to pull her once she meets them and finds out they’re not who they said they were.

It’s better to be in the game than on the sidelines, so the height lie is worth it.

However… I’ve now been informed that guys are using egregiously ancient pictures of themselves from back when they used to look completely different. I’ve seen this behavior from women, forever, but it makes sense from their side because guys are so visually-oriented as far as attraction. If a chick doesn’t have the right look, a guy isn’t trying to talk to her at all.

I didn’t imagine that guys are employing the same strategies. :/ I mean.. How are you going to send a chick a picture of when you were in shape, and show up to the date fat & nasty? o_O I mean.. What’s that supposed to get you? Is she supposed to FORGET that she was previously messaging and texting with someone that she thought looked good? 😀

Is she supposed to want to hook up with a guy merely because of what he says, his physical appearance having no bearing on the situation, whatsoever?… GEEEEEEEEEET the **** outta here! 😀

The only counter to False Advertising is to either request NEW pictures of whomever you want to talk to.. haha I guess you’d have to have them take a picture, holding up yesterday’s newspaper or something! 😀 .. or to meet up with the person ASAP, before getting too text-y with them and working yourself up into wanting to meet someone who, physically, no longer actually exists.

The Roster

Women re-entering the dating game need to recognize that unless a guy doesn’t know any chicks at all, y’all go onto The Roster, and not directly to the head of the class, as far as dating him.

For myriad reasons, some biological and some mental, guys in general find it easier to date multiple women than women find it to date multiple men.

This can be confusing to women, because their relationship to a guy can be fantastic, loving, caring, interesting, exciting, mentally stimulating, and otherwise absolutely perfect as far as she’s concerned, but he still won’t commit to her or call her his girlfriend.

This is because he’s willing to put you on the roster, but he’s not willing to fire the rest of the team for you. If you watch baseball, teams don’t have only one pitcher. They have several. Amongst that group, they have starters and they have closers. Different people are relied upon for different things. Unless a guy’s willing to rely on you for EVERYTHING he wants, there’s no reason for him to commit to you.

As perfect as your relationship is to him, he has the same perfect relationship to other women and he enjoys all of youse. Sometimes, he enjoys all of you in the same way and sometimes for different qualities that each of you brings to the table.

A guy that has several fantastic relationships has no reason to select one and eject the others until and unless one gal clearly outshines the rest of his favorites and he feels like he would be satisfied with “just” her instead of the other billion women on this planet that might be down with the program.

So.. Reentering the dating game doesn’t put you back amongst a group of suitors looking to woo you immediately into another relationship. If guys are still in the game when you break up with your SO, you’re going to have to work your way up from the bottom, not start from the top.


Assuming that a guy wants to date a woman that’s approximately his age… He’s going to have to deal with the difference between broke chicks and women with careers.

Most likely, when he kicked it to his ex, she was willing to let certain behaviors, lifestyles and ways of being of his SLIDE because she was destitute and interested in living off of his money. Fast-Forward a few years, where now he’s meeting women at after-work Happy Hours ‘n such, and now he’s dealing with women that already have their own money.

This means she’s not going to be impressed with him taking her to the movies. She can take her own ass to the movies, and pay for her girlfriends as well. He’s no longer going to be the best-dressed guy she knows. Now, she’s in the corporate world, and is around guys that dress up every day, instead of guys from around the way that dress up two nights a week to go clubbing and otherwise look like bums all the time.

Since she’s stepped up her game, she has more guys than you kickin’ it to her and she’s not as likely to go for your “I’m tha shiznit, so take it or leave it” style that worked for you when you were the only guy she knew that had a car.

Also.. Since you’re getting back in the game, you’re most likely going to be paying for the dates, which are going to become increasingly expensive as women a) get older, and b) have more sophisticated guys taking them out that you need to defeat in competition to pull her.

Essentially, unless she’s STILL broke, you’re going to have to stop relying on your gimmicks and actually talk to her. Get to know her. You’re going to have to pull her by your personality because your cars, money and house just got your foot in the door for her to listen to your sap rap at all so you can throw your hat in the ring with the other fellaz.

Unfortunately.. After spending several years with a chick that you pulled WITHOUT having to talk to her, your skillz MIGHT COULD be rather dusty, so good luck with that! 😀


Back in the day, you were a hot property. The more clothes you took off, the more likely you were to get a rap.

If you’re not staying on top of your gym game, that might work fine, so long as you stay with the same BF/GF. Once you start dating again, you’re heading down the river in a boat with no paddles, Capicse? 😀

I’m talking about men as well as women. The older women get and the more money they generate on their own, the more they trend towards how men choose women, looks and fun.

If you’re a guy looking to get back in the game and you haven’t been keeping your physique well-tuned and in tip-top shape, you’re going to be at a disadvantage, competing with the younger guys now that MILFS and Cougars are in style.

Back in the day, you had older chicks all to yourselves. Now that they’ve become a valid fetish category, you have guys 10-20 years younger than theses ladies tryin’na tap that. So you not only have to look better than dudes y’all’s age.. You have to strive for Sugar Mama status.

Anyway… Getting dates and hookups and relationships is much easier for attractive people to achieve than unattractive people. Utilize the mirror. If chicks thought you looked like El Debarge back in the day, but now, they regularly mistake you for Anthony Anderson or Drew Carey, it’s gonna be a tough row to hoe from here on out.

Career Daters

When you get into a relationship for several months or years and then return to the dating game, it’s important for you to realize that not everybody’s taking the same trip you are.

Sure, there are some people that just exited relationships like you did and are looking to get back into one ASAP.

OTOH, there are lots of people that are career daters. They happen to be “single” now because they feel like it, and not because they haven’t found “The One” yet.

In fact, they’ve found several “One”s, or Mr. or Mrs. Right Now’s. They may meet them every week.

Coming from a relationship with someone that was actually interested in only dating one person (unless, of course, the relationship ended because you finally figured out that YOU were the only one dating ONE person, hehe), you’re going to have to get back used to people that will tell you whatever they need to to hook up with you, even though they have no intention of following through with any of the dreams they’re selling you.

One of the worst things you can do is tell a career dater that you’re fresh out of a relationship and blah blah blah. That’s bait for a shark. Don’t do it. 😀 They’re going to smile in your face and tell you everything’s going to be better….. and just lay down right here…..


As upset as you are that your relationship ended, you might find yourself dating someone who’s even MORE UPSET that THEIR relationship ended and they’re not dealing with it very well.

You may be required to carry the baggage that they brought from the previous relationship.. ESPECIALLY if they got cheated on last time. You’re going to have to suffer through “Guilty Until Proven Innocent”. You’re going to have to figure out and then defuse whatever people did to them in the past just so you can get back to square one and start your relationship fresh.

It could be even worse if they’ve gone all the way through the entire process of messing around, dating, hooking up, getting engaged, getting married and getting divorced already. Sometimes, that shakes people’s belief in the system they’ve been fed since they were small children. As much as they’d like to take that same journey with you, minus the divorce part, their heart just isn’t in it.

Hopefully, they’ll figure this out about themselves before you get overly interested in a continuing relationship with them.

Still worse are the people that want to act out NOW that they’ve been cheated on or whatever. You really don’t want to get involved with someone that’s looking to do the same thing to someone else that was already done to them.

Two wrongs doesn’t make a right, but sometimes, it just feels good. >:D

Gloom & Doom

It’s not all Gloom & Doom, however. 😀

The good thing is that a lot of your friends are married or currently in long-term relationships and they’ll have friends that you can meet that they’ve already vetted. They’re going to know who’s still looking for someone to settle down with and who’s incessantly playing the field.

Another good thing is that this is your chance to learn about yourself. Take some time to figure out what worked for you in your previous relationship and what didn’t work. Figure out how that relationship changed you, who you are now as a person, and what you want from your next relationship.

Decide whether the qualities you utilized to select your ex are the same ones you’d like to use this time around. Decide whether you’re willing to give everything you gave to the previous relationship or whether you’re bringing a different set of qualities to the table this time.

In fact, starting all over is your chance to reinvent yourself and do things totally differently. You can make better decisions based on the experience with relationships that you have now.

You’re older, wiser, and hopefully BETTER-LOOKING!!! 😀 hehe Now’s your opportunity to chart the course for the rest of your life, and the sky’s the limit! >:D Connect with Bill via Facebook, Twitter, LinkedIn, MySpace, Email Subscription, RSS Feed

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  1. Thx Bill, great advice as always!!! Sometimes I feel like a naive like kid in this dating world, but I cant hide away in my cocoon forever.

    1. hehe Glad you got something out of it, Panama! 😉

      You’re programmed to be like a naive kid. It’s what keeps the wonder in dating.

      Hopefully, you’ll never lose that, because afterwards, it becomes all business.

  2. Thank you for summing up very valuable information I could have used prior to dating again. “Trust but verify”. However, my dating experiences have been the best teacher. Painful, but I almost want to thank that “smiling” person for saving me years of trial and error.

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