Red Flags: My Sweet Girlfriend & Her Dark Past
How to proceed if you are in a relationship with a woman who has many red flags and a dark past.
In this video coaching newsletter, I discuss an email from a viewer who found out while dating his current girlfriend that her body count is over 35, she worked as a topless waitress for 2 years, had an OnlyFans account with an ex, another ex was a drug dealer, she was an escort for 2 months and supposedly only had 2 clients. She doesn’t drink or do drugs and has always been loyal, honest and faithful with him. Her past with her previous boyfriends was a train wreck and she came from a broken home.
So far, her past has not affected their relationship, but he’s very concerned about the numerous red flags and asks my opinion. My comments are in bold italics like this below in the body of his email.
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I know what you guys are thinking. Everybody’s laughing in the comments now. Because the old joke is that for guys, when they tell you what their body count is, you cut it in half, and for women, you double or triple it. So, if she’s saying her body count’s 35, it could be as high as 100, potentially. We just don’t know. It’s all based upon her character. Somebody that’s an escort for two months, having sex for money, only had two clients, does that sound believable if they’re doing it for two months? Unless these were repeat clients and they kept them busy. So, I don’t know. I don’t know what the story is.
If you guys have been on the dating apps, especially dating apps like Hinge, you’ve noticed in the last several years that there’s a lot of girls on there that act like they’re there to date, but really what they’re looking for is the gullible guys that have more money than common sense, and they basically want to get paid to hang out and date and have sex with these guys. So, maybe it was something like that. And typically in those situations, the girl’s coming over, hanging out with the guy for %1,000-$2,000 a week. Something like that could keep a girl busy for the two months, but we don’t know.
So, obviously, these are some of the red flags. But keep in mind, this guy’s already in the relationship. It’s easy for us sitting here to watch it and just go, “She belongs to the streets!” So, in these situations, because these things are going to happen, you get down the road and then you kind of get a full picture of what you’re really dealing with. It’s easy for us sitting on the outside, because we don’t have any emotional ties to this one way or another to just say, she’s out. But I always say, you’ve got to judge a person by their actions, not their words. And so far, I mean, this is a little bit longer email than most, but there’s a lot of good detail in here.
My name is Bob. I’m 25, living right here, on Earth.
Well, congratulations, earthling.
My first email sent your way was titled “Am I Being Tested, Should I Just Back Off, or Both?” a little over a year ago. Since then, I’ve made a lot of progress. While I have only read the book twice, (come on man), I did at least highlight the absolute fuck out of it, have referred back to it in bits and pieces many times, and have listened to the audio version at least 40 times by now. Your work has been the foundation to my success. Thank you very much.
I’ve done quite a lot of practice over the past year and a half dating, and especially out in the bars/nightclubs, becoming familiar with women socially and intimately. As a consequence of all this preparation…
Well, remember what Confucius said, “Success depends upon prior preparation, and without said preparation, there’s sure to be failure.” So he got prepared, and then when his opportunity came, he did well. But we’re trying to determine if he made a good choice.
…when the most recent opportunity to make my move on a beautiful woman presented itself, I went for gold and passed with flying colors. Well, almost.
So, I met this gorgeous woman. Her name is Jessica, she’s 26, and we met in class studying together. We both work full time and study part time. I got talking to her pretty quickly, and about a month later I was able to nail down a walk, just me and her, after class one day and lined up a date night for the following week. We got to talking about ourselves and the common interest between us was health and fitness. I mentioned I was into lifting weights and indoor rock climbing and invited her along. This took some of the surprise out of the mix but still kept it exciting, as she’d never been before.
Coincidentally, she happened to live in a neighboring suburb to the one I had been parking my car in before catching the train into the city for class. During our time together, she proceeded to mention that she didn’t have a car and that I was “welcome to park my car in her unit’s car space.”
“You can park your car in my garage anytime, baby.” That just took me back to a girlfriend I completely forgot about. Thanks for the memory. I haven’t thought of that forever. And no, I’m not going to share.
We spent no more than an hour together that afternoon, and later that evening I received a text that said, “thanks for catching the ferry with me,” without any initiation on my part. I had also noticed that every week when I got to class, she would never fail to make eye contact with me and give me a rather big smile with a somewhat extended amount of eye contact.
So he’s taking his time as somebody he sees in class. She’s checking him out. She’s on the other side of the classroom. These are kind of fun, because you can kind of just let them happen. But if you sit there and you have staring contests and you hesitate and you don’t engage her in conversation, you just stare, she will determine that you’re a beta. You smile, you chat her up and talk. Maybe you’re selective, maybe you’re taking your time, maybe you’re taken. But you’re happy to talk to a pretty fair maiden just to see what she’s like.
So, the day of the date arrives, and I pick her up from her place that evening with little resistance on her part. I set a definite time which she complied to, picked her up and off we went to the rock climbing gym. It was heaps of fun. I was totally calm and collected, confident, steered the conversation in a lighthearted and positive direction and took the lead on everything without being pushy or stubborn. I kept her doing 70–80% of the talking, basically followed your book to a T.
After climbing, I drove her back to her place. We were talking about grabbing dinner and I playfully said, “So dinner’s on you back at your place, right?” and she said, “I’ve actually got some leftovers from last night. You’re welcome to come in and share them,” so I did.
Oh, I’m sure that’s all she wanted to share.
After we finished eating, I went for the kiss, and right after that happened, we took it straight to the bedroom and hit a home run on the first date. She proceeded to tell me this and that about how she had been curious and interested since we first met.
It’s a scientific fact that women are more attracted to men whose feelings are unclear. So, he didn’t sit there and stare at her creepily and then never approach her. He smiled, he chatted, but he took his time. And it made her wonder, “Why hasn’t he made a move? Why hasn’t he asked me out? Does he have a girlfriend? Maybe he doesn’t like me.”
So things to come were looking pretty good. I didn’t stay over that night. She flaked on me the next time I set a date with her, said she’d forgotten and made other plans. She apologized the next day and hasn’t flaked on me since.
Well, that’s good. You always look what people do, not what they say. And that’s what we’re going to have to do in this particular case.
We began dating regularly, and she mentioned that she only likes to date one person at a time but didn’t hold me to it. I was having such a good time with her that I only really wanted to see her. Slowly, we started seeing each other more often each week. Getting to class late became a recurring problem, no explanation required there.
That’s very naughty — extracurricular study activities.
I took her out to multiple/different places almost every time I saw her and still do. I plan things sometimes based on hints she gives me about what she’s interested in and have surprised her a few times with epic date nights and adventures, especially on her birthday more recently. Setting things up so as to become an unfolding of the evening like you describe in the book sure does make for a great time together.
She started showing signs of a 9 interest level about 2 months in. About a month after that, she subtly brought up exclusivity, which I picked up on and sealed the deal. It’s been 4 months since then, and things have been going pretty smoothly, and they still are.
Now, for the messy stuff… She’s opened up a lot about herself while we have been together.
This guy has spent half a year with her, so it’s not easy to just pull the plug. It’s easy for us to sit here and go, “Oh yeah, she belongs to the streets,” but we’ve got to look at her actions. Because sometimes you don’t find these things out. Like he found this stuff out about six months in, apparently.
Mostly before we became exclusive but also after, and there have been a few concerning bits and pieces of information:
· She comes from a broken family. She was kicked out of her mum’s place when she was 17. She never really had a relationship with her dad until more recently. Both her parents remarried when she was really young.
· She worked as a topless waitress at parties over a 2 year period and worked as an escort over a 2 month period, where she slept with 2 guys.
Two guys… only two. I can just imagine what the comments are like. Do you guys believe that it was only two? Was it 20? 200? Or was it really two?
· She was an alcoholic in her early twenties for a few years.
· She’s had 5 boyfriends before me. None of them ever really dated her or took her out anywhere.
But yet she still was in a relationship with them. Isn’t that interesting? The only thing it matters is how they feel about you.
One of them died from a drug overdose administered by someone else.
Sounds like she made great choices in the past.
One of them she dated for a year, and that ended when she found out he was seeing other people the whole time and had basically been lying to her about his entire life.
Well, those things will happen when there is no strong dad or masculine presence to guide her. She’s got to figure it out on her own.
One of them is a 110kg MMA fighter on steroids, who was pulling doors out and throwing shit around the unit they lived in together before she left him and got her own place. He also sold drugs to help make a living.
He sounds like a delightful human.
That one was last year, so I sure do hope I don’t have anyone coming after me. If I did, it probably would’ve happened by now, so I’m not too worried anymore. He crashed her car when they were together, and she sold it for the money required to get her new place. He cheated on his ex with her when they started their relationship, but she didn’t find out until months later when they were settled in together.
· She told me her body count is around 35.
Well, what’s the verdict, guys? Do you believe her, or not?
· She’s on her phone all the time.
· She was terrible with money and didn’t keep any savings from her prior years.
· She becomes anxious easily and used to suffer from pretty severe anxiety attacks.
· She tends to be a little insecure about how she looks. She needs a bit of reassurance when she gets worried about things.
Again, this is what happens when there is no daddy in the household.
· She often jokingly asks me things like “do you hate me?” or “are you sure you still love me?” In which case I just reassure her, and then we’re all good.
· She created an OnlyFans account with her last ex because he wanted to and posted provocative images on there without showing any actual nudity or pornographic content. She told me they filmed that stuff privately for themselves but didn’t post it anywhere.
So, it’s out there.
The account was still open after we were exclusive but had been totally inactive for a while. I told her to completely delete it asap and she did.
The important thing is she did, she deleted it. Because we’ve had plenty of emails over the last several months where women are in these situations, they get caught, and they say, “Oh yeah, I’m going to delete that dating profile,” “Yeah, I’m a delete that OnlyFans,” “Yeah, I’m going to delete my Seeking Arrangement account,” and yet it’s still active. So, in this case, she’s deleted it.
To round it all off, I haven’t exactly done everything perfectly either. She knows all about my sexual history.
Gentlemen don’t kiss and tell. It’s in the book.
And I’ve thrown around plenty of unnecessary bits and pieces of information that I would’ve been better off keeping to myself.
You slipped up. It happens.
I guess that’s what happens when you only read the book two times, right?
Well, that’s on you, bro.
She’d told me that she used to do modelling photo shoots and had a lot of pictures on her Instagram. She’s since cleaned it all up. She has 5K followers and quite regularly gets dm’s from all kinds of people trying to shoot their shot. She gets asked out pretty often too. She tells me about all of them. An incident arose a couple months ago where I asked if I could see her Instagram dm’s and check out all these messages. She offered no resistance, and I had a look through them with her.
Well, you can always delete those. It could have been the sanitized version, but the fact that you just out of the blue asked her and she says, sure, that’s good. That’s better than her going, “Why do you want to see it? This is my private stuff. You can’t see it. It’s not for you. You’re just insecure.”
I discovered she was actively talking to 6 other guys who were supposedly just friends, some of them exchanging messages once every one or two weeks, others almost on a daily basis. There was one guy in particular she had been talking to regularly who was sending her heaps of flowery bullshit with love heart emojis and stuff like that, and she was doing it back.
“You say he’s just a friend.”
I read through stacks of it before I checked out his profile, which is just filled with pictures of him almost naked from all of his modelling shoots. I asked her what the fuck she was doing and can’t believe I actually had to explain why it was inappropriate to be communicating with guys like this actively.
Well, again, no dad to teach her these things.
She explained that she’d been friends with all of these guys for at least a year, some longer, and never saw them in person.
Well, they’re not really friends. They’re kind of digital pen pals who obviously have the thirst for your girl.
At least not one on one. The message history proves this to be true, based on what I could see. I went through heaps of it. I told her never to initiate contact with them and only to reply if they contacted her first. I also said that if I was her, I wouldn’t be talking to them at all. I checked up on her about it a week or so later and she told me she stopped contacting them because it made me so uncomfortable.
A good woman will do that. She’ll say, “I’m going to respect my boyfriend’s boundaries, because I don’t want to lose this dude.”
I’ve checked her phone a few times since, and she appears to be keeping to her word.
“Trust but verify,” as Ronald Reagan said. It’s all we can do.
Now, onto the brighter side of things:
After that truckload of, “Oh my god. Holy shit, Batman, that’s a lot of red flags! Holy red flags, Batman!”
· She’s confidently told me that she’s never cheated on her partners. She’s said when she’s had enough, she ends the relationship and moves on. She took time alone to herself to process things after her last relationship ended and didn’t plan on getting into another one any time soon. That changed when I came along because things went so well.
Well, of course. You’re just an awesome human being. Because you’ve got a great coach.
· She’s super ambitious. She’s already opened a business on the side and is creating an income using the skills and qualifications from the course we just finished together. She’s held down her new job for this entire year and has a promising plan for where she wants to take it over the next few years.
· She lives alone, we hang out at her place all the time, it’s kept neat, tidy and in order.
· She’s working hard in the gym and wants to compete in a girls bodybuilding competition next year.
Just don’t get too masculine, because then she’ll start looking like a dude. It’s such a turnoff.
· She’s ambitious about building up wealth through a property portfolio and wants to have a loving family in the future.
· She’s done an exceptional job at managing her finances over the entire year.
· She seems to be open and honest about everything. She’s told me all about herself and doesn’t seem like she’s hiding anything.
· She’s heaps of fun to hang out with, she’s got a good sense of humor and we laugh and banter really well together.
· She enjoys spending time with me doing the things I love to do like training, spending time in nature and going out to places here and there for fun.
· She’s really good in bed…
Well, obviously. She had a little experience.
and absolutely gorgeous.
He sent a picture and she is. And he’s a handsome dude, too. He kind of looks like “Superman,” the one in the nineties. So, it’s not going to be hard for him to find somebody else if he has to move on.
We have sex 2–3 times per week on average. Sometimes more especially when it first kicked off. Never less.
· She’s extremely kind to me…
That’s super important.
…proves to be very reasonable and she has a very supportive nature. She’s a great communicator.
· If I ask her to do something for me, she does. She cooked really nice food for us, helped me out with errands and got me things I needed when I asked her to. She even surprised me with a logo she’d made for a business I’m just starting to put together.
· She doesn’t smoke or take drugs. She is focused on her health and fitness, so while we go out from time to time together, it’s no longer a major part of our lives, which is refreshing.
· She never yells at me, reacts in extreme ways or starts arguments.
Super important — easygoing, easy to get along with, right?
The most that tends to happen is that she needs to vent about something on her mind that’s bothering her. There was one instance where she was extremely pissed off with me about something and it still did not become an argument. I use the communication skills outlined in the relationship phase of the book and everything gets resolved without much trouble, if any at all.
Well, when a woman feels heard and understood, the legs open, and when they don’t, the legs close. And she’s able to communicate without turning into a hothead. That’s a good sign.
· She’s put a lot of work into herself through therapy,
Now, most people will not do that, so that’s a plus as well.
…as well as different avenues of self-help over the years. She has overcome so much of the trouble that affected her in the past. It’s a common interest between both of us. We both really appreciate the resources and information we share with each other. When she started inquiring about how I was able to create such a loving, effortless relationship between the two of us, I informed her of your book. She was really impressed and has since mentioned or referred your work to a few friends, as well as one of her work colleagues.
Well, thank you to the Misses. Much appreciated. Referrals are always appreciated.
The title of this email is a bit of an oxymoron; despite all the red flags, I haven’t actually had to do much to help her out.
Her attraction level towards me totally appears to be in the 9–10 range, and so is mine towards her. I love her and she loves me too. She’s told me that I’m the best boyfriend she’s ever had, and that this is the first time she’s had such a healthy relationship. No one feels smothered or underappreciated. We are both comfortable having space from each other without creating any drama.
Very, very important.
Time spent on the phone is kept to a minimum, and everything gets shared when we see each other in person. We always have such a good time together. I’ve put a lot of work into building a stable, supportive relationship with her. When I look to the future, I only see things getting even better than they already are.
She is also, easily, the most beautiful woman I’ve ever slept with. She’s sexy as hell. My body count is 8 and she is the most recent. It would totally break my heart to end this relationship, and if I do, I am not simply going to find someone else who is ready, open, available, with a high interest level and as kind, sexy, fun, loving and supportive as her.
It won’t happen right away. It takes time. It might, but in my experience it always takes way longer than you expect. You’re probably going to be waiting a few years for that to happen. But, maybe not. Maybe your number is up. Maybe you’re a little further in line than the rest of us who have experienced the ebbs and flows of life. Great loves, great friends, great business opportunities, they don’t come along very often.
I have had one of the best years of my life to date being with her. However, I cannot comfortably continue seeing her without consulting you on the matter. I’ve listened to plenty of your email newsletters where you have mentioned guys just like me in situations with girls that have completely undermined their man’s trust and ruined their lives, or severely wasted their time and energy. There was one you answered recently about a guy that found out his girlfriend was actively cheating on him 3 years into their relationship, when he found pictures on her computer and had previously suspected nothing.
Well, in that particular email, he found the pictures, the nudes that she had kept, and it was in her cloud. And so, obviously what was going on there is she claimed it had only happened one time, and she never told him because she knew he would dump her, which he did once he found out. And what I mentioned was the fact that she kept all of those pictures, even though she’s supposedly in a relationship, she kept the incriminating evidence.
So that told me, on some level, she really liked that guy. She’s in a relationship with somebody else, but she still goes back. Because the tab was open on her computer, and that’s how he ended up seeing it, and she had passed out. So, she has these open, even though things are great in their relationship, looking at her having sex with this other guy. So, it’s not like she’s deleting that and moving on, she’s having some kind of fantasy. Who knows? Maybe she’s still talking to the guy. It doesn’t really matter, because that chick belonged to the streets.
I honestly, seriously doubt that anything like this is going on with my relationship, but how will I ever actually know?
Time and repetition. You’ve got to spend enough time with her and see what she’s really like. And you’ve only been with her six months. It’s still early.
The guy in that email probably felt just the same way I did before he found out what was unknowingly happening to him. I honestly don’t care what she’s done before. I just need to be able to feel confident that the relationship is being built on as stable a base as I feel it is. Trust, but verify, right?
Well, so far, I haven’t seen any behavior that would show that she’s still this person. She seems to be operating with integrity, which in these other emails they have not. Like the girl who supposedly just cheated one time, but she still had all the pictures open. She still cheated.
Three years the dude gave to her. Never, ever a red flag, no problem ever, and she cheated. And if those pictures would not have been there, he would have never discovered them, and he would have never known, and he probably would have married that girl. And she would have gotten away with it. Unless he eventually found her cheating before. You just don’t know. You do the best you can. You’ve got to collect all the data you can, so you can make an intelligent, informed decision.
I can choose to stay and continue building up the loving relationship that I have, or I can choose to go, slowly build my game back up and prepare for the next potential partner I may find, however long that may take. I love her, I don’t want to let her go. Just because she comes from the streets, does that really mean she still belongs there?
I would really appreciate it if you respond to this email and help me make the right decision moving forwards.
Well, if she belongs there, she’ll behave that way. And I haven’t seen any behavior since she’s been with you that would show that that’s still part of her life. It seems like she values you, based on her actions. And the fact she’s so open with her phone and everything else, it’s as Ronald Reagan said, trust but verify. That’s all you can do.
In this particular case, it’s just this one only because she’s been so forthcoming and open, I would give her a chance. But again, you’ve got to trust but verify. It’s only been six months. People can hide who they are for about the first 90 days. So, you’re at about three months and kind of seeing the real her. What happens in six months, or a year from now, or two years? Then you can make an intelligent, informed decision. All you can do is see how it goes, take it day by day, and live in the present moment, because that’s the only moment that really exists anyway.
So, from what you shared, it looks like that part of her life, she’s left behind. She’s gone through therapy, she’s done the work on herself, and 97% of the people ain’t going to do that. She is doing that. So, if it was me, if I was in your shoes and I had the same experiences you had, I would give her the benefit of the doubt until she screws it up. That’s all you can really do.
Because based on her actions and the fact that she’s always done right by you, she’s earned your continued openness to her continuing to prove herself to you that she is this person that she’s been representing and doesn’t have all these weird secrets going on in the side, like a burner phone or something like that. But you don’t know. If she is that, eventually at some point she’s going to slip up and you will find out. And if that does happen, I assume you’ll be sending a future email.
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 and book coaching session with yours truly.