It can be challenging to be a challenge even when a woman is not connected to your daily life…

I mean, when you have high interest in a woman, all you want to do is text her, ask her out, meet up with her, and tell her how much you like her.

And you want to do it right now so she doesn’t forget about you!

So, sitting back and waiting isn’t easy…

Yet, a woman’s interest in you goes up the MOST when she’s thinking about you and wondering what your next move will be between dates; not on your actual dates. <==Read 3x…

So, we have to give her that time away from us, be a challenge, and take slow, measured steps forward instead of trying to rush things along if we want her interest to go up instead of crashing into the ground at some point.

Well, as I’m sure you know, that’s easier said than done…

And that’s one big reason why it works – it’s hard to do and shows that you have self-control and high levels of internal strength.

Plus, being a challenge also signals that you are a successful guy who might even have more than one option in terms of the women he can choose to be with. =)

So, being a challenge is important if you want a woman to fall deeply in love with you instead of losing interest in you at some point and it’s always difficult to be a challenge when your interest in a woman is super high…

But what if you see her every day?

What if you have some classes with her for the whole semester at your university, you work with her (*not recommended to date co-workers but that’s a different topic), she’s in your friend group, she works at a place you frequent, or you do volunteer work with her every day?

Is it possible to be a challenge with a woman if you see her all the time?

And, if so, how can you make sure you’re allowing her interest to go up instead of smothering it?

Well, that’s exactly what top student J.J. asked me about the other day…

Here’s what he wrote in:

“Hi Jim,

I have followed you for a few weeks…your advice has helped me a lot.

I have one problem with one woman:

How can I be challenge if I see her often, like every day…?

Let me know what you think.

Thank you,

J.J.”

And here’s what I told him:

How to be a CHALLENGE when you see a woman every day…

Hi J.J.,

First of all, of course it’s more difficult to be a challenge with a woman when you see her every day vs. a woman who is more of a “stranger.”

I mean, it’s better if she can think and wonder about you without seeing you around too much…

And spending too much time together too soon is one of the easiest ways to kill romantic attraction, even if you’re pretty good at doing things right with a woman.

That’s why I recommend shorter dates at first and waiting until she’s fully in love with you (her interest in you has climbed to 9/10 or higher) and she’s your official girlfriend before you take her on a weekend trip.

Too much time together makes it very difficult to be a challenge and almost always smothers the embers of a budding fire of female interest inside a woman instead of stoking them into a giant bonfire like we want to do.

So, when you see a woman every day, being a challenge is difficult.

However, it can definitely be done.

Here’s a key distinction to keep in mind:

There’s a difference between the time you spend on dates and simply seeing each other around…

More about this later.

And then, secondly, here are a few tips that can help with this specific situation:

1. Talk to other women (and guys too) and try to make them laugh when she’s around but not too close…

You want her saying to herself from a distance, “What’s all that fuss over there about?”

Of course, you don’t want to be a clown; just a fun guy who can make women laugh.

And you don’t want to overplay this – make it seem natural and casual as much as possible (hey, even better if you’re just the kind of guy who makes people laugh).

Don’t look over at her to make sure she’s watching or anything.

Just organically make other women laugh when she’s around as much as you can.

2. This is key: Don’t avoid her but don’t put too much focus/attention on her either…

Be normal and polite with her and try to make her laugh sometimes as well.

Playfully tease her a bit if you can.

Just don’t give her most or all of your attention whenever you see her.

3. Don’t compliment her too much or tell her that you like her “that way” or tell her how much you like her…

Just show her that you like her with your ACTIONS (more on this in a second).

4. Here’s another big difference between this situation and when you meet a woman you aren’t sure you’ll ever see again:

You want to take things even SLOWER with a woman you know you’ll see again; especially if you see her a lot/every day.

So, normally, you would ask for a woman’s number during your first conversation with her…

However, if you know you’re going to see her every day for the next 6 months, you don’t want to ask for her number so soon.

Play it slower and a bit cooler and wait at least a week or two before you ask for her number.

Then, of course, you MUST ask for her number or give her yours (like you always do when you’re interested in a woman).

You just don’t do it as soon as you would otherwise.

Make sense?

Excellent.

Slowing everything down even more than we normally do (which is already slower than the way most other men out there who rush into rejection approach things) is the main way you can be a challenge with a woman you know you will see frequently.

You still take action to move things forward; you just take slow, measured steps forward instead of rushing and, when you know you’ll see a woman a lot, you go even s l o w e r.

Counter-intuitive.

Absolutely.

Effective?

Well, I highly encourage you to find out for yourself. =)

5. Ask for her number or give her yours and then ask her out on a date – asking her out shows her that you’re interested in her romantically (so does going for a kiss by the end of the second date. So you do this instead of talking to her about your feelings for her/attraction to her)…

This is how you show romantic interest – you ask her for her number and then ask her out on a one-on-one date outside of the situation where you normally see her.

Not by randomly “telling her that you like her” one day.

Now, if you have a university class with this woman, then you want to ask for her number almost like it’s an afterthought.

It’s no big deal – it’s just what people do.

Smooth and natural.

You can just hand her your phone with the “add contact” screen open and turn away from her a bit to remove some of the tension. She knows what to do.

Then, just send her a short text immediately so “she has your number also.”

For example, you can just text her your name. It doesn’t matter much what you text her, just keep it short because the purpose of this text is simply to make sure she has your number as well.

That way, when you contact her later, she’ll know who it is…

And it allows her to chase you as well if she wants (by texting you first, etc.).

This is a very effective way to ask for her number – very smooth and chill. It leads to less tension and this is important when you know you’ll see her a lot.

Nobody wants awkward moments so we’re going to make it less awkward for her. =)

Now, if you WORK with this woman, first of all be very careful. I highly recommend not dating women from work. But if you decide to do it anyway, I highly recommend that you give her YOUR number instead of asking for hers…

This puts the ball in her court and protects you from potential problems at work (it’s not harassment if you give her your number and then she starts texting you first OR she just never texts you and you move on).

So just write your name and number on a piece of paper and hand it to her and then walk away and see if she texts you sometime after that “so you have her number too.” If she does, great. If she never texts you, move on.

And then, if you’re in a friend group with her and that’s why you see her a lot, just make sure you don’t ask out more than one woman in that group…

If you do that then they’ll think you’ll just ask out any woman who’s reasonably attractive and that they’re not special when you ask them out AND it will make the second woman you ask out think she’s your second choice from the group, etc.

Remember: You can take your shot with one woman in each social circle you’re in.

Maybe 2 if you wait long enough after the first one didn’t work out and your attraction to each other is mutual/grows over a period of time and/or if the group is large and not that close.

Otherwise, don’t ask out multiple women from the same friend group.

They can all ask you out if they want; but you have to either keep them all as friends (casual hookups can sometimes happen) or pick ONE to date. =)

And then lastly:

6. After your first date with a woman you see every day, wait 4-8 days before you ask her out on the next date like always

The difference?

You have to be cool about everything during that waiting time – when you see her act normal.

Be totally comfortable waiting to ask her out again – be cool about it.

When you see her, don’t avoid her; you can have fun with her, etc.

Just don’t ask her out again too soon – this is the biggest part of being a challenge.

And it’s harder to do if you see a woman every day, especially if you have super high interest in her.

But this is what gets you “all the way home” with her in terms of HER interest in you; so you’re going to do it and you’re going to be chill about it.

When you see her, it’s no big deal…

Yes, you had a great time on your date and you like each other.

And YES you’re going to ask her out again.

You’re just going to wait 4-8 days before you do it unlike every other guy she meets and eventually gets rid of.

Because you’re a WINNER. =)

So it doesn’t matter that you see her a lot (as long as you don’t make it weird/awkward when you see her) – what matters is that you wait before you ask her out on the second date just like always and that you don’t tell her all about your feelings for her etc. just like normal.

And if she can’t take the tension anymore and she comes toward you by touching you the next time you see her after your date, kissing you, reaching out to hold your hand, putting her arm around you, etc., allow her to do it.

Or, if she asks you when you’re going to go out again, reward her for that and say, “Are you saying you want to go out with me again?” And then if she says, “Duh….” Then you say, “How about Wednesday at 7:30? Does that work for you? There’s a new wine bar I wanna check out – maybe we can head there.”

If she presses you like this about hanging out again, you can ask her out before that 4-8 day window comes up; otherwise we’re waiting just like we always do.

And if she asks you out directly at any point, accept her date invitation (say yes) or give her a counteroffer if you can’t make it.

HER: “Wanna go to a movie with me tomorrow night?”

YOU: “Yeah, that sounds cool.”

OR: “I’d love to but I can’t tomorrow night. Can we do it on Thursday night instead?”

*The only exception to this is if she asks you to hang out that same day…then you say, “I’d love to but I’m busy tonight. Can we hang out tomorrow night (or Thursday night etc.) instead?”

So that’s how you handle it when you see a woman frequently and you still want to be a challenge with her.

If she’s interested in you and available, this will work assuming you also do everything else we talk about inside the Attract and Keep Her system

And, if she’s not interested in you, it won’t work like always – then you just have to smooth things over with her and not make a big deal out of the fact that it didn’t work out between you so the whole group doesn’t have to suffer through an awkward situation every day.

So the last thing I should say about this is to be super cool about it if things don’t work out with her – if you see her a lot you don’t want her or the people around you to feel awkward just because you tried to date someone and it didn’t work out the way you wanted.

Alright sir, good luck and let me know how it goes…

Until Next Time,

Jim

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Jim
Jim

Jim Wolfe is on a mission to help you permanently solve your dating and relationship problems on the way to helping 100,000 men live their ideal life with their ideal women and helping to increase the percentage of happy, healthy relationships from 30% up to 40%. Jim has been studying dating and relationships from the male perspective for over 17 years. Now, he has clients in 72 countries and counting and is the author of the "Attract and Keep Her" best-selling dating and relationship system for men.