7 Ways to Take Initiative without Scaring Him off ...

7 Ways to Take Initiative without Scaring Him off ...
By Lyndsie • Aug 22, 2025

In matters of love and relationships, a lot of things have changed. Naturally, it's totally acceptable for girls to go after guys, to ask them out, to take the lead – but that particular dance is ever changing, and you have to be careful of the steps. Not everything is equal, because so many guys out there seem to scare easily, or to get intimidated if a woman comes on too strong. It's no wonder that so many girls and women alike are still looking for ways to take initiative without scaring him off – and this post can help with that!

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1. Flirt with Him

Flirting is still the most surefire way to take initiative without scaring him off, although you do have to be careful. You don't want to be over the top with your flirting under any circumstance, because typically, less is much more. You don't want to smother him in attention, but a few long looks, some well placed, curious questions, and even the occasional wink and smile will let him know you're interested.

  • Absolutely! In fact, many guys appreciate it when women take the lead sometimes. It can show confidence and interest, which is really attractive.

  • Keep it light and fun. Suggest a date or plan something you know he enjoys. It doesn’t have to be a big gesture, just enough to show you care and are interested.

  • Not necessarily. Some people are just more passive or shy. If it bothers you, have a gentle conversation about it. Communication is key in any relationship!

  • Yes! Many guys find it refreshing. It takes the pressure off them and shows that you're equally invested in the relationship. Just remember to balance it out, so it doesn't feel one-sided.

  • Give him some time and space. Sometimes, people just need to adjust to new dynamics. If he’s interested, he’ll come around. If not, it’s his loss!

2. Be Yourself

So many girls make the mistake of transforming themselves into someone they think their crush or boyfriend would like, which ultimately leads to a relationship founded on lies. That might sound melodramatic, but just think of how awful it would be to have to pretend to be someone else for such a long time. If a guy doesn't like you for who you are, he's not worth it anyway. The best way to take initiative is to be true to yourself, to be yourself, and attract him that way.

  • Absolutely! In fact, many guys appreciate it when women take the lead sometimes. It can show confidence and interest, which is really attractive.

  • Keep it light and fun. Suggest a date or plan something you know he enjoys. It doesn’t have to be a big gesture, just enough to show you care and are interested.

  • Not necessarily. Some people are just more passive or shy. If it bothers you, have a gentle conversation about it. Communication is key in any relationship!

  • Yes! Many guys find it refreshing. It takes the pressure off them and shows that you're equally invested in the relationship. Just remember to balance it out, so it doesn't feel one-sided.

  • Give him some time and space. Sometimes, people just need to adjust to new dynamics. If he’s interested, he’ll come around. If not, it’s his loss!

3. Be Outgoing

It can be hard to be outgoing, especially if you're shy. While a lot of guys out there like their ladies shy and retiring, being upbeat and outgoing is still a great way to take initiative without scaring him off. You don't have to be loud and you should avoid being obnoxious; you don't need to hog all the attention in every situation, either. Rather, when you're around the guy you like, just put yourself out there, join in the conversation, and again, let your true self shine through.

  • Absolutely! In fact, many guys appreciate it when women take the lead sometimes. It can show confidence and interest, which is really attractive.

  • Keep it light and fun. Suggest a date or plan something you know he enjoys. It doesn’t have to be a big gesture, just enough to show you care and are interested.

  • Not necessarily. Some people are just more passive or shy. If it bothers you, have a gentle conversation about it. Communication is key in any relationship!

  • Yes! Many guys find it refreshing. It takes the pressure off them and shows that you're equally invested in the relationship. Just remember to balance it out, so it doesn't feel one-sided.

  • Give him some time and space. Sometimes, people just need to adjust to new dynamics. If he’s interested, he’ll come around. If not, it’s his loss!

4. Avoid Clinging

Clinging will generally scare a guy away. For that matter, it scares girls away as well; I hate clingers, you know? If you don't want to scare him away, you have to avoid this at all cost. Show how strong and independent you are, and how well you're able to stand on your own.

  • Absolutely! In fact, many guys appreciate it when women take the lead sometimes. It can show confidence and interest, which is really attractive.

  • Keep it light and fun. Suggest a date or plan something you know he enjoys. It doesn’t have to be a big gesture, just enough to show you care and are interested.

  • Not necessarily. Some people are just more passive or shy. If it bothers you, have a gentle conversation about it. Communication is key in any relationship!

  • Yes! Many guys find it refreshing. It takes the pressure off them and shows that you're equally invested in the relationship. Just remember to balance it out, so it doesn't feel one-sided.

  • Give him some time and space. Sometimes, people just need to adjust to new dynamics. If he’s interested, he’ll come around. If not, it’s his loss!

If you're looking to engage your partner in intriguing conversations, why not try some hypothetical questions for couples? These fun queries will not only keep the conversation lively but also stimulate deep thoughts and potentially reveal insights about each other's personality and thought processes.

5. One Step at a Time

A lot of the so-called “expert advice” says that one way to take the initiative is to let him control the pace of the relationship, but I don't agree with that. Unless that's your preference, even relationships in their infant stages should be a series of compromises between the two of you. However, it is a good idea to take things one step at a time. Don't start planning marriage – and worse, making it clear that you are – with your new crush. Don't force things to happen ahead of time, and make sure you know what his comfort levels are, too.

  • Absolutely! In fact, many guys appreciate it when women take the lead sometimes. It can show confidence and interest, which is really attractive.

  • Keep it light and fun. Suggest a date or plan something you know he enjoys. It doesn’t have to be a big gesture, just enough to show you care and are interested.

  • Not necessarily. Some people are just more passive or shy. If it bothers you, have a gentle conversation about it. Communication is key in any relationship!

  • Yes! Many guys find it refreshing. It takes the pressure off them and shows that you're equally invested in the relationship. Just remember to balance it out, so it doesn't feel one-sided.

  • Give him some time and space. Sometimes, people just need to adjust to new dynamics. If he’s interested, he’ll come around. If not, it’s his loss!

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6. Short and Sweet

While you might be tempted to show your crush or boyfriend the notebook full of love poems you've written while pining away for him, don't. The best way to take initiative without scaring him off is to keep things short and sweet. You can absolutely let him know you've been interested in getting to know him, but don't show him that folder that has your name paired with his in new and interesting ways scrawled all over it.

  • Absolutely! In fact, many guys appreciate it when women take the lead sometimes. It can show confidence and interest, which is really attractive.

  • Keep it light and fun. Suggest a date or plan something you know he enjoys. It doesn’t have to be a big gesture, just enough to show you care and are interested.

  • Not necessarily. Some people are just more passive or shy. If it bothers you, have a gentle conversation about it. Communication is key in any relationship!

  • Yes! Many guys find it refreshing. It takes the pressure off them and shows that you're equally invested in the relationship. Just remember to balance it out, so it doesn't feel one-sided.

  • Give him some time and space. Sometimes, people just need to adjust to new dynamics. If he’s interested, he’ll come around. If not, it’s his loss!

7. Tell Him

Last, but most certainly not least, just tell the guy how you feel. Being honest is always the best, even if you're subtle about it. Remember, the worst he can say is no, and if he doesn't want to go out with you, then you're undoubtedly better off without him anyway.

There are lots of ways to take initiative without scaring him off, but some of them are specific and will be up to you. Every guy is different, and what seems scary to one might be perfect for another. What are your favorite ways to take the initiative with a new guy?

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Where Thoughts and Opinions Converge

I like this guy, but we're really good guy friends and he probably thinks of me as just a friend. How do I get out of that?

I like this guy who is in some of my classes at school and I think he like me to. We would flirt alot and he would hold my hands if I turned around to talk to him during class. Anyway I feel like he doesn't like me the same way because when some of my friends would tease him about liking me (we do that alot to eachother just to annoy eachother) he acted embarresed and said eww. :/ I'm so confused! What should I do?

Hi :) you can just call me J :3 So this is a complicated thing.. I like this guy but I've only seen him twice before and he's shown signs that he may like me but he's nice to everyone so I still don't know. Anyway, he's actually my close friend's brother and I told her that I like him a while ago and she was fine with it :) but the problem is that i feel like if im going to flirt, etc. It would be weird with my friends around. And plus he is the nice guy but I think he's shy and 'inexperieced' in this sort of stuff but he's allowed to date now but he's two years older and according to my friend I'd have to join their church if o want to date him so what should I do?? Because im faithful to my religion as well but im just confused what to do!! Thankyou and I hope you will reply back :) P.s sorry that was very long!

I commented but now I don’t see it

I like this guy who is in a class I take once a week. We've hung out in group situations and he Always sits next to me in class. In between Classes we email and sometimes text quippy little things to each other and other girls from class think he's into me. I've been trying to ask him out in a coy way...but I don't think he is getting it, he tends to just ignore it. I would just accept that he isn't into me, but I get the vibe that he is definitely flirting with me. He also has made comments about how I am on a different level looks wise than him (he is a bit of a nerd and definitely shy) So I don't know if he just thinks I am out of his league or what. What Should I do?? I can't stop thinking about him!

hey. i really like this guy and I met him through my friends but the problem is my friend likes him but he told me he doesnt like her. I dont know if I should go after him because technically my friend saw him first... but he's really nice and sweet. We pretty much talk everyday at lunch but we dont have any classes together cuz he is taking lower classes... I was also wondering if i should offer to tutor him?? I dont want to make him think Im too easy though...

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