11 ways to pursue a woman without looking desperate

We sometimes include products we think are useful for our readers. If you buy through links on this page, we may earn a small commission. Read our affiliate disclosure.

The best way to go about pursuing a woman is always to be confident and be yourself. 

But if you do find yourself in the position of having feelings for someone and not being sure how to get her attention, then this guide will help! 

In this post, we’ll cover 11 ways you can go after a woman without coming across as desperate. 

1) Offer advice on something she’s struggling with in a non-intrusive way

If a girl you like is struggling with something and looks to be in need of advice, offer her your help in a non-intrusive way.  

The majority of girls don’t want pity.  

Your best bet for this would be to casually approach a woman and tell her about your own struggles in the same field, but give her tips on how to overcome her obstacles. 

This way you’ll show her you’re not afraid of admitting your weaknesses, and that you’re not putting up any false pretenses about how confident you are in the topic at hand.

And if she does need your help, she’ll readily accept it without hesitation.

2) Create a connection by showing an interest in her hobbies 

Here’s an interesting fact:

Humans are inherently social creatures. Maybe that’s why you can feel lonely even when you’re surrounded by dozens of people.  

The thing we all have in common is our love for hobbies and interests.  

Everyone has things they love to do, whether it’s taking photos, playing music, or even just chilling out on the couch watching movies.  

And that’s why making genuine questions about a woman’s passions will help you connect with her and show her what a cool person you are.

  • “What’s your favorite book? I was thinking about reading it the other day.”
  • “I love that band. I saw their show last week and it was awesome.”
  • “How long have you been taking photos? Can I see them?”

These are just a few examples of questions that will lead to an awesome connection. And the trick is to show an interest in her hobbies and make it clear that you enjoy doing the same activity.

3) Listen to what she says and ask follow-up questions

Another effective tip is to pursue a woman without looking desperate by listening to what she says and asking questions about it.  

Everyone likes being listened to, and being around a guy who cares enough to not rush her will instantly make her feel more comfortable in your presence.  

Pro tip:

Avoid the “me too” trap.  

If you approach a woman and start talking about an experience you had, but she has a completely different experience with it, then don’t say “me too.” Say something like “Yeah I’ve had that happen before. How did you handle it?” This way, she knows you’re actually interested in what she has to say.

4) Compliment her on something unique about herself 

It’s normal to compliment someone when you like them. The key, however, is to make sure it’s not a generic compliment.  

It’s easy to go the cliche route and say something like, “You’re beautiful.” But all she’ll hear is that you’re telling her she’s pretty, which isn’t all that meaningful.  

Instead, try something unique about her appearance or personality that you genuinely admire. For example, “I love your glasses. Did you design those yourself?” or “I love how you speak in public. It’s so cool to see a woman so fearless.”

The key to making this work is learning how to do it without coming off as fake. It’s hard to recognize when you’re doing it, but the best way is to observe yourself and make note of the times you compliment her without even realizing what you were doing.  

It will take some time, but practice makes perfect!

5) Ask her to join you in a social activity that she might enjoy 

This one’s a bit trickier to pull off, but if you do it right, it can totally make her feel special and show her you’re a genuine person.  

Think of a social activity she might enjoy, like going to a local craft beer festival or something similar.  As you talk with her face to face, casually ask her if she’d like to join you in it sometime. 

Don’t ask too early, but don’t wait too long either. The best time to ask is after you’ve just met or are just starting to build up some rapport with her.

Here’s the step-by-step process:

  • Make sure you’re comfortable with the activity. For example, if you’d normally be scared to go to a craft beer festival because of your fear of drinking and getting drunk, it wouldn’t be a great idea to mention it when you first meet her.  
  • Make sure you don’t get overly enthusiastic about it. If you come on too strong and sound like a salesperson, then there’s a good chance she’ll feel like she can’t say no.  
  • Give her an out if she doesn’t feel like going.  
  • Ask casually, without being too pushy or unable to take a “no” answer.  
  • Follow up with a question about how she feels about the idea and if you should put it on your calendar.
  • Make it clear that she doesn’t have to come, but that you’d love to hang out with her if she’s interested.  

6) Be a good listener

If you want to pursue a woman without looking desperate, then being a good listener is the way to go.

All women love talking about themselves.   

Many girls will feel reluctant about doing it, however, because they don’t want to be judged or intentionally ignore what the other person is saying.  

But if you show that you’re genuinely interested in what she has to say and that she feels comfortable with you, then she’ll have no qualms about telling you all about her life.

Also, remember that you’re not just a listener. When you’re listening to her talk about herself, be sure to make it clear that you’re following along and that it’s interesting to you.

7) Get to know her friends 

How can you make a connection with a woman and make it seem natural if you don’t even know any of her friends?

And yet, not knowing them is the biggest damper on a potential connection. The thing is, women love talking about their friends and family. It’s like an instant connection when they can share all the good things going on in their lives.   

So, if you want to pursue a woman and make it seem natural, then casually ask about her friends and family.  

Doing this will give you the opportunity to get some insider info on her life and make it seem like you’re just naturally getting to know each other.

Make sure you don’t spend too much time on this tip, though. You don’t want to come off as overly intrusive or too focused on one area of her life. The art of pursuing a woman without looking desperate is learning to balance it. If you focus too much on one thing, then you’ll come off like a creep.

8) Treat her as an equal

Many guys treat a woman as though she’s the prize. They put her on a pedestal and treat her like she has every right to demand things from them. But it’s important not to do that.

Why?

Women have a completely different mindset than men.  They don’t think of things in terms of what they deserve, and they don’t think of themselves as being owed anything by anyone. They believe that everything they get is earned through their hard work and talents.

That’s really not the way it works. Not only that, but a man holding a woman on a pedestal gives her the wrong impression about who she is and how she’s supposed to act in the relationship.  

Rather than treating her as a prize, treat her as your equal. Respect every decision she makes and listen to her opinions like they’re just as important as yours.

9) Take the lead for a little, but then step back and let her take over

This one’s really easy and works really well.

All you have to do is ask her a question, like “What do you think we should do next?” or “Where should we go for dinner?”

Then, take her answer and run with it!  Follow up on what she says, regardless of how crazy or unreasonable it sounds. You want to show her that you’re able to follow through on something.

Once you’ve done that, though, let her take the reins. For example, if she says “I know a great Thai place,” ask her where it is and then let her lead the way.

It’s important to do this because you never want to make her feel like a kid in a candy store. If you feel like she’s the one in control, then she won’t feel like you’re just taking over.  

Also, don’t forget to connect with her on an emotional level. Show how excited you are about the activities you’re doing, but also make her feel as though that’s what she should be excited about as well. Show her that you’re both on the same page and that you both share the same passion for what you’re doing together.

10) Let her know you’re into her 

OK, I know what you’re thinking:

If I tell her that I’m into her, won’t I look desperate?

Yes, it might make you look a little desperate. But, it’s going to come off more like you’re simply expressing that you find her attractive than that you’re desperately chasing after her.   

The key is to let her know in a subtle way. You want to show her that you’re genuinely into her, but you don’t want to come off as overly creepy.

You can do this by simply playfully teasing her about being into her. You can tell her little things like, “I have a thing for blondes,” and then add in a goofy smile.

Or, you can do it during a break in conversation with something like, “You know what? I’ve got to say, I’m totally digging you.” Again, do this with a smile.

That’s about all you need to get the point across. You can even take it a step further if she seems interested by saying things like, “I’m having a great time with you. In fact, I was thinking that maybe we could have dinner sometime. Would you be into that?”

11) Show appreciation for what she does and make her feel welcome

The last step is, of course, how you show appreciation for what she does and make her feel welcome.

The thing is, most guys don’t do it. But this will make all the difference when it comes time to get more serious with her.

You want to make sure that she thinks you’re a standup guy and that she feels really appreciated when you’re together.

This might seem like a lot of work, but what you’ll find is that as you continue to use these tips, they actually become second nature to you. You’ll know how to pursue a woman without looking desperate because that’s how you act when you’re with her.

And the best part is: 

She won’t even be able to tell the difference between you acting like this and just being a normal, chill guy! But if she does pick up on it, then she’ll definitely appreciate it.

Final thoughts

So there you have it.  

The art of approaching a woman without looking desperate is actually quite simple. It’s learning how to balance it and apply it in the right situations. 

And once you’re able to pull off this skill, then women will see that you’re able to get what you want without coming off as desperate and she’ll start flirting with you more often.

But if that doesn’t happen, at least you know what not to do. Simply follow the tips that I mentioned above.

Just remember, being a man means knowing how to approach a woman and getting her attracted to you without looking desperate. You’ll get more opportunities with women and you’ll be able to start the relationships you want without feeling like you’re just wasting your time.