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

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

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.

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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.

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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.

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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.

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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.

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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.

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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

  • katkat

    2012-03-06T23:41:20.000Z

    hi! so i really like this guy...he is SO HOT. ive heard he thinks im hot and i sometimes catch him checking me out, we even grinded at homecoming! but we never talk..we really dont know each other. but i wish i did!! what do i do to try and make something happen between us?
  • Anonymous

    2012-03-01T08:41:57.000Z

    He's leaving next week and he likes to go out with me and I said sure, but haven’t invited me yet. I haven’t heard from him for days, what should I do? should i just wait for his response?
  • Patricia

    2012-03-02T17:18:51.000Z

    Hi im 18 my name is Patricia have a crush on this guy, and i think he does too cause he tried touching my hand, and talks to me, he dropped a bottle cap on purpose I took the first step and started talking to him, how do i know if he likes me when we just been talking for 2 days?
  • Angela

    2022-04-23T13:18:28.132Z

    Hello my name is Angela So… I’ve recently got out a long term relationship with my ex boyfriend of 11 years… I ran into this guy a couple months after the break up, he’s sweet, handsome and caring but the only thing that kinda bugs me is that he doesn’t take initiative to things. For example: I always have to ask him can I see him instead of him saying “I want to see you” Then if I want to go out to eat I have to ask him, he doesn’t come out to say it etc… I see him a couple times throughout the week because our work schedules are different but it’s always sexual whenever I do see him. He claim he likes me & wants to be with me but it’s like I’m starting to question is it just sex or is it something more! He said he doesn’t like clingy females but at the same time he claims he wants to be around me. And I don’t want to be doing too much. I’m confused and need advice
  • Anonymous

    2012-06-08T04:13:46.000Z

    There is a guy that used to go out with my best friend and she broke up with him because he was really clingy, but I still talked to him for awhile after. He really liked me and told me several times and always made me feel good about myself, but he started being really clingy with me so I yelled at him and told him to leave me alone and he has tried talking to me a couple of times since then and I told him to leave me alone each time. My boyfriend broke up with me a couple months ago and I really miss talking to the other guy, but I am afraid that contacting him now might make me seem horrible, and I am also worried that he might be just the same as he was before. What do I do?
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