My Family Says I’m Dating & Sleeping With Too Many Women!

Some things to consider if those close to you don’t support your personal life.

In this video caching newsletter I discuss an email from a viewer who has dated and hooked up with 15 different women since he broke up with his fiancé a year ago. His female family members and friends say he posts too many different women on social media and he’s sleeping around too much. However, he’s getting more women than ever, but some of them become entitled and develop an attitude and he blows them off.

He asks my opinion. My comments are in bold italics like this below in the body of his email.

In this particular email, the guy broke up with his fiancé about a year or so ago. He’s been using what he learned in my book to meet and date quite a few different ladies. He sent a whole photo library of his roster, all very cute, very fit, very in-shape women.

So all of his females, I guess, his sisters, his mother, his aunts are all not too happy because the other thing he’s doing is he’s posting a lot of these girls to social media as he’s dating them. Plus, the other thing that he’s running into is that his family members are saying that he’s spoiling these girls, he’s spending too much money on them, and after a short period of time, they develop an attitude, and he doesn’t like that very much. So he dips and he moves on to the next one.

So the women are saying, “You’re going to get a reputation as a fuck-boy if you keep posting this there. You’re going to have a hard time getting dates,” and he’s like, “Well, quite frankly, I’m getting more dates than ever,” and it’s not been the case, but obviously he’s getting some women that are kind of getting a little arrogant, a little entitled. There’s some hint that maybe he’s a little bit too nice to some of these women when he likes them.

So let’s go through his email and see what’s going on here.

Viewer Email:

Hi Coach,

I am a YouTube member and have recommended your work to many of my mates which they also watch and love your content. Many of my mates have read your books and know you keep it 100.

I have a question for you and something my family of females and best mate says to me a lot, “Be careful posting a ton of girls on your Instagram as you will get a bad name for yourself Bob.” I am very open in what I post on my business page as I use it as my personal page also saving switching from one to the other, my mate on the other hand posts solely business and golf.

I mean, at the end of the day, it’s a scientific fact that women are more attracted to men whose feelings are unclear, and also women like you more if you’re popular with the ladies. However, if you’re not, if you’re not attached to anybody and you’re kind of a free agent, then you’re also dating women that you really like and that you want to have a relationship with, that can create some problems. If you’re just having unattached, no-strings attached sex and hanging out, having fun, and hooking up, it’s pretty clear you’re single and ready to mingle, you should be OK with it, but if you’re dating a girl or trying to date a girl seriously, and you’re constantly posting pictures of other women, that’s not a good way to go about it.

So I suspect what’s happening is he’s going from girl to girl, and he posts the pictures and he leaves them there. Like I said, when you run into trouble is if you’re dating a bunch of different girls and you got a couple that are candidates for potential relationship, and then they see your social media, they look like they’re a rotation girl, then you’ll end up blowing your chances, especially if you come across a good woman who was raised right.

Now, one of the things that I noticed about a lot of the pictures that he sent was when you see lots of tattoos, especially big tattoos that cover large parts of their body, that’s typically indicative of women that got issues. In other words, it’s like the more tattoos they tend to have, the more crazy they tend to be. It’s not always 100% the case, but tattoos, big tattoos in very obvious places, like their whole leg is tattooed up or their whole arm or whatever, the more you see the incidence of that, the higher you’re going to see incidents of kind of nutty behavior. Also piercings, the more crazy the piercings get and the more numerous also can be red flags.

So it would appear that a lot of the women he’s dating and hooking up with are girls for fun and fucking, but not really family-oriented girls. So if that’s all he’s really dating and he’s into, it’s not going to really be that big a deal, but if he starts dating a girl that’s family-oriented and was raised right by her dad, she’s not going to put up with you going through a lot of women, her just being one of the girls that you’re boning. Even if you really like her a lot, if you’re posting evidence of you dating other women while you’re dating somebody else, that’s not going to go well. If the pictures are older pictures of other women that he dated months ago and you’re only posting pictures of the girl you’re currently dating, you should be OK. I’ve seen plenty of instances where guys are just posting every girl they go out on a date with, and they’re trying to date other girls because they’re trying to use their social media to make girls jealous. That’s the wrong way to go about it.

So if you’ve got a history of datin lots of beautiful fit and in-shape women, and you’re dating like one at a time in sequential order, you should be OK, but again, if you’re dating a girl you really like and you’re posting pictures of other women that you’re also dating and sleeping with, that’s a bad way to go. You will cock-block yourself. So from that perspective, your sisters, your mom and everybody else telling you not to do it, that is correct, but it just appears, from what he sent me, that he posts the pictures of the woman he’s currently dating, hanging out, and hooking up with, and then when that doesn’t work out and he moves on, then those pictures stay there and whoever he’s dating in the future, then he’ll post pictures of her on there.

So it looks like the way he’s going about it is he’s doing it tactfully and it just looks like, “Hey, this guy’s dated a lot of beautiful girls.” So it’s just important not to rub other women in their face. You want her to feel special. You want to feel like she’s the only one that you’re dating and into at the time.

I have been told numerous of times stop posting so many dates and women on your Instagram and business page as it comes across like you are a f**k boy and will get a bad rep that women will run from!

Well quite frankly, the women that I see are the type of women that are going to be really into this anyways and they’re going to have the attitude of, “Oh, I can make him mine,” but again, from what I saw, it looks like he’s going in sequential order and not just posting a bunch of random women all at once, all at the same time.

To be honest, Coach, I disagree massively in the regard of women running away from me as I seem to be getting more and more dates and quite easily tell them upfront what I want and they respect that and by the first or third date, we are both cumming like the Niagara falls.

Well, that’s another thing that is different. He’s telling them up front, “Hey, you know, I broke up with my fiancé a year ago, and I’m just casually dating. I’m not looking for anything serious. I’m open to it, but I just want you to know where I’m at. I’m still healing. I’m taking my time.” Remember, women like a guy that’s a challenge. If she thinks that she’s going to have to work to get you, I mean, the bottom line is they like you more if they have to do that. If you make it too easy, you’re too nice, you’re too soft, then you’re going to get blown off or you’re going to get friend-zoned.

So everything I’ve seen so far, this guy’s doing a really good job of maintaining that balance. He’s being honest up front and he’s having good interactions and in good relationships with the women that he’s talking to, at least so far. Unlike the other video newsletter that I did this morning, Are We Dating The Same Guy & Tea Apps That Shame Men, this guy is doing a good job. I don’t see the same problems that he’s not having, the same problems that the other guy was having where he’s got a bunch of women coming out of the woodwork going, “He’s an asshole. He’s a jerk.”

In my opinion, what woman doesn’t love to be wined and dined and then to have great sex with the anticipation slowly building over dinner with a massage afterwards with, of course, plenty of preheating the oven with foreplay and then the final gift of Some Chunky Cheung Fun?

Chunky Cheung. He’s from the UK. I haven’t heard that one before. Chunky Cheung fun!

The only problem I have and agree with is my family of women and best mate keeps telling me, which I agree with, but don’t know how to stop doing it or what way to go about it is, “Stop wining and dining these women as you are spoiling them,” and what does spoil mean? But to ruin. don’t spoil your woman as they are becoming spoiled brats, then expect it and begin to have an attitude and become entitled witches.

Well again, just the pictures of the women, they’re very beautiful, very attractive, but I notice a high incidence of big tattoos on them. So big tattoos typically are indicative that they came from a broken home or don’t have a good relationship with their dad. So if you lead with your money, then you’re going to attract women that are expecting you to spend big bucks on them.

At the end of the day, what are you looking for? Easygoing, easy to get along with, she’s flexible, she’s a giver, she’s nice to you. Easygoing, easy to get along with. If you take a woman out and you wined and dined her, it’s like when I go out, even when I was younger, I like to go to a nice dinner, I like eating, I like breaking bread. My friends, family, every close girlfriend I’ve ever had in my life. It’s one of the things we love to do, is to go and break bread with people we love. So if you can afford it, then you should do it and not feel bad, but if you’re going and taking her to expensive dinners, then fly them around on your private jet and taking them shopping and buying $2,000 purses and things like that, I would not recommend doing stuff like that.

Again, as the book says, you should only be buying gifts for women that are your girlfriend or your wife, and you don’t want to overdo it, but if you’re going out, you’re taking women to nice dinners and stuff like that, and you hook up for a few weeks and all of a sudden their attitude changes, they become a little belligerent and they’re not nice to you, well then you gotta dip. It’s as simple as that.

Again, like I said, just from the pictures, it looked like I see lots of big tattoos on several of these women. So that tells me they probably came from a broken home. So yeah, that would make sense that they start to act a little loony after a few weeks. That’s why I say all the time, there’s women for fun and fucking, and then there are women for family, and a lot of the women that this guy is hanging out and hooking up with are for fun and fucking. They’re not family-oriented girls, and that’s why he’s having difficulty with them.

It pains me to say they are all right as it has happened with the majority of the women which I can’t stand as it quickly turns me off them.

Well, the whole point of dating is to vet for character. It’s got to be easygoing, easy to get along with and nice to you. If they’re nice to you for the first couple of dates and then they turn into an insufferable cunt, they’re nasty and they’re rude to you, well you just move on.

Something to consider going forward for the emailer is that you’re going out with a lot of women that come from broken homes. Therefore, if you’ve got a high incidence of women copping an attitude after a few weeks, expecting you to buy them things and blow money on them, then you know you’ve got to think about, where are you meeting these women? How are you finding them? Because if you’re looking for a good, family-oriented girl, you want somebody that loves her dad. If she respects her father, she’ll respect you and respect other men. If she comes from a broken home and hates her father or says she hates men, then you’re going to have a hard time with her. So you got to pay attention to those things.

So I suspect some of these women, he’s sticking around a little bit too long and not moving on from them quickly enough, because he’s sticking around and he’s seeing the bad side of them. Luckily he moves on, he doesn’t get attached, but I would say think about the bait that you’re using to catch these women where you’re fishing. Think of yourself is like a fisherman.

I ask the question, does she want me for me, or the things that I am providing such as dinners, hotel stay-aways and the like?

OK, so if you’re taking women that you’re just casually hooking up with on really expensive trips and you know deep down you’re probably not going to get serious with them, that tells me you’re leading with your money and your wallet, and you shouldn’t be doing that. Simple dinners and simple dates are fine until she’s your girlfriend, and only after she’s proven herself that she’s easygoing, easy to get along with, nice to you, has a good attitude and loves her dad. Then you know when you’re serious, you can take her to expensive stays. If you’re taking her around, blowing lots of money and throwing money around like it’s nothing, you’re going to attract women that basically have a hooker-like attitude.

So there is truth in what your friends and family are saying, but like I said, I think you should probably be a little bit more selective in who you date. Also, you shouldn’t be blowing lots of money on expensive hotels and stuff like that with somebody you’ve been out with three times. It’s too much, too soon, because if you start taking a girl on your private jet after two dates, she expects it. So it should be the kind of thing she doesn’t even know you have a private jet. She shouldn’t really know what you do the first few dates until you get to know her. You can give her some vague answers a little bit, because you got to vet for character, and not every woman deserves to know you on that level, but the fact that he’s asking these girls that, like you’re not going to get a straight answer anyways, especially from a chick that’s a mercenary.

My best mate Bob said, “You shouldn’t have to ask your dates or girl you are dating to pay for something. She should just instinctively know to.” He stated, “Pay maybe for the first four dates or let me be generous and say five, but after that ask yourself within the five dates has she paid for anything? If the answer is no, then don’t see her ever again.” 

Yeah, if you’ve gone out on five or six dates and she doesn’t even buy a round of drinks, say you go to a restaurant and you’re waiting for your table to open up, you’re on a wait list, you have a glass of wine. The buzzer goes off, “Oh hey, our table’s ready.” A woman who’s a giver will say, “Oh, you always take me to nice places. Let me get these round of drinks here,” or they’ll buy you something and bring it over with them. Like small little gifts. They’ll do things for you.

So you got to pay attention. A woman who’s flexible, who’s a giver, she’ll want to contribute as well. Once you start hooking up, she comes over, she’s not coming over empty-handed. Maybe she brings a snack or she’s like, “Oh, I found this in the store and I thought it was so cute. It reminded me of you. I wanted to get it for your house.” It may be just a candle or something, but that’s what women do. They like you, they buy things for you, they offer to pay for drinks.

My female little cousin and auntie even said, “From my point of view, for you moving forward is to also seek counseling to help grieve your mum. Your jumping from woman to woman and it’s not healthy too. You jump in and spoil them and it’s giving them spoiled attitudes that makes them think they have the authority to talk down to you. Love works both ways equal. Please take my advice and live for the happiness of you, not pleasing woman. Find something your passionate about and chase it.”

So again, it definitely looks like in many cases he’s leading with his money and he’s spending way more money than he should on these women, which I agree with his family. You should not be leading with money because you’re going to attract women that are with you for those things.

“You’re going to make a name for yourself and you’re not that person. You’ve been brought up to be a gentleman and have good values. Sleeping around and seeing different women isn’t you. It’s not healthy. Work on yourself, pray to God and he will give you your happiness you deserve.”

Coach, any advice or personal stories are always valued. Here are some of the type of women I have dated this past year from breaking up with my long-term partner and fiancé at the end of last year, so it’s been one year exactly I have plowed through roughly 15.

Bob

So it’s a little more than one woman a month. My critique, what I would have to say, which I’ve already said in the video, is stop leading with your money. Stop taking girls on expensive trips. I would only take a girl on an expensive trip if she’s your girlfriend and you’re serious about her. So from that perspective, it looks like some of these women you shouldn’t be going out with at all.

Again, if you’re looking for stable, happy, healthy relationship, big, giant tattoos covering their body, coming from a broken home, I mean, those should be obvious things. It’s nice that you’re able to to hang out, have fun, and hook up, but if you’re looking for a serious relationship, you’re clearly going out with women that you shouldn’t be going out with. On top of that, you’re leading with your money. Other than that, with the social media and the way you’re posting, it’s working for you. So I wouldn’t do anything like that. If you’re looking for a long-term relationship, be a little bit better and a little bit more selective in who you date, and focus on making sure they have the values that you’re looking for, and of course, that they were raised right. Don’t linger around too long. Other than that, sounds like you’re having a blast. I mean, the women that you sent are very beautiful, but again, several of them, I can tell why you’re having trouble with them because again, the big tattoos kind of give it away.

So, if you’ve got a question or a challenge and you’d like to get my help, go to UnderstandingRelationships.com, click the Products tab at the top of your screen on any page, and book a coaching session with yours truly. Until next time, I will talk to you soon.