How to Date a Woman Who Has Only Dated Assholes

You know the story: Boy meets girl. Boy falls in love. Girl has no idea how to accept the love because she’s only dated assholes her entire life. Years of social conditioning are at work. Maybe her dad was an asshole, maybe her mom married one. She’s been told “when a boy is mean to you, it means he likes you” since her earliest days on the playground. Social psychology and evolutionary biology are playing themselves out as some studies suggest that women are attracted to men who exhibit certain traits — specifically narcissism, Machiavellianism and psychopathy — in short-term mates. You can chalk it up to a myriad of intersecting factors like bad role models, poor choices, self-esteem issues, shame, trauma and trust issues that feed the self-destructive cycle, like Ouroboros, the snake forever eating its own tail.

As a woman very familiar with the cycle (and assholes), I’m here to assure you that cracking open the cage around her tiny, Grinch-like heart isn’t impossible. But there are some things I want you to know about the process. If she’s worth it, you’ll be willing to do what it takes. If you’re already thinking, “No thanks, too much work,” you might be right — or you might be an asshole. Anyway, if you’re still up for giving it a shot, here’s what to keep in mind…

You don’t need to fix her.

I interviewed 20 women who made the transition from dating assholes to dating what I would call a “good guy” and almost across the board, when I asked them what changed they said, “I started to value myself more.” A lot of this is her work to do, and if she’s self-aware, she’ll recognize that. The best partnerships are two whole individuals that come together and lift each other up, not two people desperately clinging to one another.

Know your worth.

If you’re self-aware, you’ll take a look at your part. Ask yourself: Is this is a pattern for you? Are you attracted to women recently released from rehab or fresh out of an abusive relationship? Do unavailable women that reject you and take you for granted appeal to you? Women can be assholes, too. Many men who fall in love with women incapable of accepting their love could probably be labeled as co-dependent or have some kind of savior complex. All these patterns stem from self-esteem issues of your own and it would behoove you to take a good, hard look at the underlying reasons that drive the behavior.

Go. Slow.

Get to know one another before you have sex. In fact, insist upon it. When a man wants to wait before we’re intimate, I know he’s special. That doesn’t mean you can’t take the chemistry for a test ride with some light petting, but a little bit of chastity goes a long way in setting you apart from the men who just want to swipe and fuck. Willingness to wait for the physical signals that you’re a serious mate — not another disposable, predictable fuck boy.

Get rid of your dating apps.

I realize this might be counterintuitive from the whole “go slow” thing I just mentioned. But if you two are serious about giving whatever budding romance might be occurring a fair shot, imho, it’s best to reduce the amount of temptation you’re exposed to and minimize insecurity in the early phase.

Case in point: A fascinating pattern emerged when I interviewed the 20 women. They either met their now significant other and knew instantly, or they were friends for years or decades and one day, that friendship turned into something more. Only one person told me the story, “We met; we were dating other people for a while; and then decided to lock it up.” And in that instance, he wasn’t ready, and she gave him the space to become ready over the course of years. “But from that day on,” she says. “He has spent every single day making me feel important.”

Still, I think if you’re serious about the potential relationship, choosing only to date each other while you figure out if this is something more than just a fling builds a lot of early trust.

Do things during the day.

Dinner and a movie are great, but day dates say, “I want to see if someday we can do errands together.” You can’t possibly comprehend how refreshing it is when a man suggests going to a museum or on a hike. It also says that you’re willing to give her those precious, daytime work hours and that she’s a priority.

Actions speak louder than words.

If she’s primarily dated assholes, she’s used to playing games. Don’t play games. Games are for children and the kiss of death for a burgeoning relationship. Don’t wait 24 hours to text when you want to reach out to her that night. Don’t get wasted and disappear. Call when you say you’re going to call. Make plans and don’t flake. Go out of your way to do nice things for her.

That said, don’t go overboard and smother her with your love. Be assertive, but not a dick. Let her know she’s a priority, but don’t be too compliant. There’s a very thin line between reliable and annoying. It’s is a delicate balance between coming on too strong and reassuring her that you’re not going anywhere — the defining difference being your level of neediness and her level of willingness to receive love.

This might sounds like games, but it’s not, it’s a dance. Let her know you’re there and allow her the space to come to you. Be confident that she will.

Open communication is everything.

I asked every woman, “How did he make you feel safe to open your heart to him?” Over and over again, they offered some version of, “Open communication from the beginning.” Mary, for example, says, “He wasn’t afraid to express himself or tell me how he felt.”

For me, however, it’s different. Whenever I’m in a relationship with a “good guy,” I have a really hard time receiving compliments and words of affirmation at first. I’m so used to being negged or put down that I had to tell one of them to “get a journal” to log all the nice, romantic things he wanted to say to me, but I wasn’t ready to hear. I could feel his love for me, but for some reason, every time he’d try to express it, I’d feel a surge of resistance, shut down and get in my head, criticizing every little thing about him. As my therapist says, “Intimacy is your nemesis, and being hypercritical is a defense mechanism.”

So if you’re sensing a pattern of her becoming aloof or cold, talk to her about it. After all, every time you have a conversation about your fear with each other, that vulnerability will only make you closer.

Trust isn’t implicit or reciprocal.

This brings me to the juicy stuff: Baggage. We all have it. Some more than others. My therapist also said, “Love triggers all your trauma.” If that sounds awful, I’m not alone here. Multiple women expressed having moments of completely shutting down or wanting to run away in the early stages of dating their now husbands (in most cases). Most women have experienced some form of psychological abuse, verbal abuse or sexual abuse, and dating men who employ insidious forms of gaslighting have often left us traumatized and deeply suspicious.

In other words: Just because you might blindly trust her because she’s given you no reason not to, doesn’t mean she’ll be able to give you the same in return. Trust is earned, slowly, over time and with consistency.

Time is your best friend.

Patience is everything. In the same way that you can’t force a flower to bloom, you can’t force someone who is used to being guarded to open her heart over night. Check in with her. Really hear what she’s telling you and hold space for her to process what she’s feeling without needing to find a solution. She’s probably terrified, so keep it simple. “He texted me every day and asked questions about me,” Mary says. “Genuinely trying to get to know me. And he’d mentally take notes on things like the type of wine I liked or the food I didn’t like.”

Again, a lot of this is her work to do — not yours. Learning not to suffocate a man’s affection and optimism with suspicion and accusations is a daily practice for me. I constantly have to choose love over fear, and believe me, it doesn’t come naturally.

Temper your expectations.

Self-esteem is an inside job and there might come a point that you realize she just isn’t ready for you. That’s okay. Someone else will be.

A final word about “nice guys”: I’ve known a lot of men who fancy themselves as nice guys who got shit on by women. I know one of them myself. There was even a moment when I nearly fell in love with him. When I balked because I was afraid, mostly of hurting him, he blocked me on social media and cut me out of his life. This kind of behavior doesn’t lend itself to me thinking that you’re a nice guy. It leads me to believe you’re an asshole who didn’t get what you wanted. It also doesn’t build trust or create bonds — it destroys them.

Good guys behave like good guys even when they don’t get what they want. In fact, it’s the mark of a good man. I’d define a “good man” as someone emotionally stable, reliable and willing to put your needs before his, not all the time, but a lot of it.

In general, if you find yourself saying, “I’m really a nice guy.” You probably aren’t.