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When you’re meeting women regularly, you’re bound to find—and sometimes even fall for—women, younger and older, who already have boyfriends. It can be a frustrating, confusing experience. There’s nothing quite like connecting with someone who turns out to be attached.

In these situations, you have two options: move on, or try anyway.

But making the decision between resignation and pursuit can be difficult. What’s the protocol? What’s the move? And is it acceptable to chase a girl who already has a boyfriend?

Key Takeaways:

• Understand your motives and the ethics of pursuing a woman in a relationship.
• Evaluate the implications of her breakup and the potential challenges.
• Emphasize the importance of setting healthy boundaries and cultivating a strong, independent persona.
• Foster a meaningful connection through shared interests, positivity, and respectful physical touch.
• Recognize the complexities and moral considerations involved in such situations.

Pursuing a Woman in a Relationship: Understanding Your Motives

Before you go any further, you have to ask yourself why you want a girl who is already spoken for. With over three billion women in the world (and more than a few of them living within 50 miles of you), what makes this one so special? Why this one?

Is she your ex? Because you should check out our guide on how to win her back first.

If you have a compelling answer to “Why this one?” then there might be a good reason to pursue her. If you don’t—if there isn’t anything particularly outstanding about this person—then you already have a reason to respect her circumstances and move on. We’re not here to tell you when and when not to pursue a girl with a boyfriend, only to consider whether there’s a good reason.

If you do choose to pursue her, then next thing you must understand is that the process won’t be easy or always pleasant. Going after a woman who is already attached comes with a few built-in problems.

Considering the Implications of Her Breakup

Even if she wants the relationship to end, it will be difficult and painful for everyone involved. It might even be too painful for her to be with anyone in the short term. What’s more, people’s feelings are highly unpredictable immediately following a breakup. So while she might be interested now, or six weeks from now, she could easily change her mind. You just don’t know how things will shake out after the breakup, no matter what the situation is when you meet.

But let’s say everything goes exactly according to plan. She and her boyfriend break up, she tells you she’s madly in love with you, and the two of you start a relationship. Terrific, but there’s a common problem. You might wonder if there’s another guy around the corner trying to get her to break up with you. You’ll always wonder if the relationship is going to meet the same fate as the last one she was in. This might be rational or irrational, likely or unlikely—but the fear just might linger.

That’s some serious baggage to have to work through, and it can have a corrosive effect on your relationship. Here, as in most relationship challenges, sharing your concerns and discussing them openly will be essential. But it can also lead to some nasty residual fears. The quality of her character — what kind of person she is — should guide your feelings about her post-break-up.

Evaluating Your Intentions: Love or the Challenge?

The desire to be with someone because you can’t imagine being with anyone else is very powerful. But so is the desire to be victorious.

As men we want to prove we’re better, stronger, or more attractive. We want to demonstrate our ability to subvert an existing relationship for our own validation.

These aren’t fun feelings to acknowledge, but they’re crucial to recognize because they’re inherent to the male experience. We must understand our motivations whenever we pursue a woman, especially when there’s someone else in the picture.

That should be one of your guiding questions. Are you chasing a woman to make yourself feel good, or because you must be with her?

The Ethics of Pursuing Women in Relationships

We’re not here to dole out philosophical advice. But we will touch on the larger question of whether it’s acceptable to pursue a girl who is already dating someone. In short, sometimes it is, and sometimes it isn’t. Once again, your motivations will help you examine the ethical aspect of chasing a girl with a boyfriend.

All practical considerations aside. If a girl is in a relationship that is unhealthy, abusive or toxic, don’t shed tears about breaking it up. You should, however, think long and hard about the implications of inserting yourself into a toxic relationship (and dating someone who would enter one). At the end of the day, you probably can’t “save” her, so check any part of you that wants to. All you can do is be a supportive, caring friend, let her know that you’re interested, and hope she chooses you. But getting involved in a toxic relationship is also a bit like a quicksand pit. The harder you try to get her, the more enmeshed you become in her toxic relationship. This will sap your energy and make it harder for you to be a strong, healthy person.

There’s also a big difference between having a boyfriend and having a serious boyfriend. A guy she’s kind of been dating for a couple months isn’t quite the same as a guy she’s been living with for the last five years. In the former case, it’s not a big deal, ethically speaking, if you make your move and the guy isn’t a close friend of yours. In the latter, you need to seriously consider your reasons for chasing her — and determine whether you both want to pursue this relationship.

Navigating the Moral Complexities in Love and Relationships

There’s one overriding condition that, in our book, generally gives you carte blanche to pursue a girl no matter her circumstances. If you feel that you must be with this person, and — this is essential — the feeling is clearly mutual. That is, she feels about you the way you feel about her, and you both want to be together. Then you can and should go for it. That doesn’t mean it’s the “right” relationship, or that the transition will be easy. It certainly doesn’t mean that your relationship will work out. But ethically speaking, two self-aware adults choosing to be with each other despite any previous attachments is a reasonable ground upon which to build a relationship. In that case, of course, you’re both pursuing each other.

But there also strong reasons not to pursue an attached woman. If a girl is in a relationship that makes her happy, why would you want to break it up? (Again, we return to the question of motivation.) The odds of you successfully breaking her up without doing some shady things you’ll later regret are pretty slim. And besides, if you really like this person, shouldn’t you be happy for her? There are excellent reasons to be friends with women, and — as we often say on the podcast — female friends are essential to a well-rounded social life.

So consider the practical and ethical considerations here. Again, we can’t tell you what to think, feel or do. We can only share the right questions to ask so you can make sound decisions for the long term.

Understanding the moral complexities in love and relationships is crucial, but so is having the confidence and skills to navigate them. Whether it’s sparking a new connection or deepening an existing one, the art of conversation plays a pivotal role.

What if you could transform every interaction into an opportunity for a meaningful connection?

Imagine no more awkward silences, no more cringey small talk, just electrifying conversations that create a real spark. This isn’t a distant dream—it’s a tangible reality Check out Conversation Magic, and let’s turn those stumbling words into smooth, confident dialogues that leave her eager for more.

Cultivating Love: Strategies to Win Over a Woman with a Boyfriend

If you’re going to get any woman to fall in love with you, it needs to be from a place of strength and confidence. Falling in love is what a woman does to herself when you’re not around, so you need to be comfortable with periods of silence and not seeing her. That gives her opportunities to miss you and think about you as an option.

You also need an abundance mentality. That is the mindset that there are tons of women out there who you could start a relationship with. That will help you maintain the perspective and attitude you need to get a girl with a boyfriend to fall in love with you. Because it is true. There are tons of women out there you can date if things don’t work out with this girl.

But your abundance mentality is part of a bigger picture. You need to put yourself first when wooing anyone, especially a girl who already has a boyfriend. In practice, that means having time for her only when you actually have time for her. Don’t let your work, your passions, and hobbies, your self-improvement, your gym routine or any other part of your life suffer because you’re trying to get a woman who already has a boyfriend to fall in love with you. The best and most attractive thing you can offer her right now is your strength and independence from her situation. Running every time she says she needs you will erode that strength and independence.

Setting Healthy Boundaries in Complex Romantic Situations

Setting boundaries is crucial if you want a woman to fall for you. It’s doubly important when you’re trying to get a girl to fall in love with you and she already has a boyfriend. If you’re nothing more than a shoulder for her to cry on, she might love you. But she won’t be in love with you. You’ll be her friend, the guy she calls to complain about her relationship. But you won’t be the man she considers as a partner.

In general, it’s a good policy to separate yourself as much as possible from whatever relationship she’s in at the moment. But if you do want to lend a sympathetic ear or offer advice, make sure that it’s on your terms and when the time is right for you. Don’t drop everything every time she needs to talk. She will lose respect for you because it shows her you don’t respect your time and your life. And a woman can’t fall in love with a man she doesn’t respect.

As with any woman, when you’re trying to get a girl who has a boyfriend to fall in love with you, building a connection is essential. Presumably, if you want a girl who already has a boyfriend to fall in love with you, you’ve already made some kind of a connection with her. But you can always do more to deepen the connection you already have and push it toward romantic love. That, more than anything, will give her a compelling reason to be with you.

Being a Beacon of Positivity in Her Life

One powerful way to be there for her while simultaneously creating attraction is to make her laugh. Don’t underestimate what a laugh means to a girl — especially one who is struggling with her relationship. Making her laugh, being playful and joking around give her a subtle refuge from what she’s going through at home. You don’t need to have “heavy” talks about what her relationship is like to be supportive. You just have to show her a good time. It’s those visceral feelings that will eventually move her to choose you. This is especially important when you’re texting because one of the fundamental rules of making a girl like you over text is to keep it light and playful. Just be sure to avoid the most common texting mistakes as well.

At the same time, she might not be getting a lot of interest in her at home. One hallmark of bad relationships is that one or both parties start feeling unappreciated. She might have totally forgotten what it feels like to have a man want her. Making her feel appreciated and desired might be the emotional step you need to spark romance between the two of you.

What’s more, she might be in a relationship with a guy she no longer has much in common with. If this is the case, play to your strength in having more in common with her. Not superficially, but emotionally, intellectually and creatively. Oftentimes in long term relationships, one partner becomes disinterested or out of step with the passions of the other person. Celebrate your common interests—whether it’s a brand of humor or a side project—to deepen attraction and make you more desirable. Remember, your goal isn’t to manufacture interest. This would be disingenuous, manipulative and potentially worse than the dynamic of the relationship she’s already in. You want to be unapologetically excited about the things you two share.

Utilizing Body Language to Express Romantic Interest

Finally, and on a very practical note, don’t forget the role of touch. Once your emotional and intellectual chemistry is developed, you must find a way to express your physical interest in her. Without a physical component, you run the risk of being the shoulder she cries on when her relationship is bad. Or just an escape from her bad relationship.

Touch sends a clear message that you’re interested in her sexually, and not just as a friend. It also allows you to test her interest in you, and to slowly, respectfully, move the boundaries of your existing relationship forward. Pay attention to her eye contact when you’re with her to gauge how interested she is. If she reciprocates, then an attraction is almost certainly developing between you. And if you’re feeling ambitious, you can turn her on over text.

In short, getting a woman in a relationship to fall for you is very difficult, complex and far from guaranteed. It can also be more trouble than it’s worth. But for rare cases where you can’t imagine being with anyone else, it can absolutely be worth it.

Remember: If she’s your friend, you’ve already made the most meaningful connection of all. Now you just need to shift that a little bit and the two of you can have something even more than friends. Whatever you choose, continually return to the why. Your motivations and her feelings, more than anything else, will be your guide in this challenging but important dynamic.

Want to Effortlessly Attract the Girls You Want to Date?

Let’s face it, you’re killing it in your career, but when it comes to charming the socks off a stunning woman, do you feel like you’re just winging it? Imagine this: you walk up to her, hearts racing, palms a bit sweaty, but this time, you’re armed with more than just good looks and ambition.

What if I told you that with the right tweaks to what you’re already doing, you’ll tap into your natural charm? No more awkward silences or cringey small talk. We’re talking electrifying conversations that spark a real connection, making her eyes light up with excitement.

This isn’t just talk—it’s your new reality. Check out Conversation Magic, and let’s turn those stumbling words into smooth, confident dialogues that leave her eager for more. Ready to be as impressive in your love life as you are in your career? Let’s make it happen!

Featured Snippet Question and Answer:

Question: Is it acceptable to try to win over a woman who already has a boyfriend?

Answer: Pursuing a woman who is already in a relationship is a complex and sensitive matter. It can sometimes be acceptable, depending on the nature of her current relationship and your motivations. Before proceeding, it’s crucial to consider the ethical implications, your intentions, and the potential impact on all parties involved. Successful pursuit requires a respectful approach, emphasizing genuine connection, setting healthy boundaries, and navigating the situation with care and understanding.