With Men and Women and Dating, Who Should Initiate?

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Let the Man Lead

“Dear Ronnie – The Dating Coach for Women,

I hope you can give me some advice. I met a guy online – he contacted me, who I really like (in all ways!) We have a great connection, its very relaxed, there is obviously a physical attraction, he is very respectful yet fun and kind, etc.

Our first date went really well and we ended up chatting until early hours of morning. We then organized catch up the following Friday (my suggestion to pencil in that day) During the week in between he suggested dropping in twice, but I was ‘busy’ both times.

He then came down to spend two hours on the beach with my daughter and I at  his suggestion. We caught up Friday night, and it was probably the best date of my life – fun, sexy, relaxed, free, easy etc. He sent me a message the next morning saying “Thanks for a great night!”

I didn’t hear anything for the rest of day Saturday or on Sunday, (although I know he is active on the dating site). So I sent a message to him end of Sunday to ask how was his weekend and got a nice reply – friend-like and easy going. That was it. Mine message was a little flirty and left room for him to take that opportunity to ask me out again, but he didn’t. Just a nice reply, and a ‘sleep well’

So, I actually have next weekend free without my daughter and would really like to see him. I was going to leave it until tomorrow night if haven’t heard from him and then contact him (and maybe see if he would like to catch up Saturday). Or should I wait entirely until he contacts me? He doesn’t seem at all to be one to play games, and actually mentioned the other night (cheekily) ‘where was my initiative’?

I’d love your advice please,
Diane in Durham”

Dear Diane,

The question of who should initiate is complex and people have all sorts of opinions. This is my take on the best way to handle at least the first 4-5 dates. After that, things can loosen up a bit because you are starting to become an “item” and dating is on the brink of moving into the first phase of relationship.

So here are the different opinions – I’ll list them each separately

1. Let Men Initiate

What I have seen to work best time after time is to let men initiate in terms of asking you out. I often refer to ballroom dancing to illustrate my thinking. In ballroom dancing, you can only have one leader and one follower if you want to dance well. Otherwise two leaders produce a power struggle and two followers means you are going nowhere.

That’s why I recommend holding off on initiating anything, from calling or texting or asking men out. Don’t do it.

2. Ask Him Out Only Once

Some women feel they will lose their minds if they don’t ask a man out. So I tell them, well I don’t want you to lose your mind. Do it ONCE. Then see if he picks up the ball.

Sometimes a man will just be curious, but then once you do spend a little time together, the rare guy who needs this kind of nudge will think, “Hmmm, I like her and want to see her again.” So he asks you out. But the last thing you want to do is pursue a man. Never ask a man out more than once. If you do, don’t expect him to ever take the lead – he’ll think why should he when its clear you are willing to do all the work. And if that idea doesn’t bother you, well more power to you.

Most women start to get irritated with a  man who never takes the lead. To prevent this irritation ladies, don’t take the lead in the first place. Simple as that. If you do, you will likely find a man who is a bit more passive and willing to let you be in the driver seat on everything. While that might have advantages, most women get annoyed sooner or later.

3. I Like a Woman Who Initiates

Some men seem to think the woman needs to prove herself by showing she’s not afraid to take the lead. In some cases, these men tend to be egalitarians, wanting things to be balanced and equal.  They are willing to take turns but not shoulder the responsibility. This is probably more related to younger guys for the most part who today are under 40 or 35 even.

This is a small percentage of men. And some of them have a chip on their should about women from being burned, rejected or taken to the cleaners from divorce. Personally, I’m a little leery of this type of guy.

4. If She Likes Me, She’ll Initiate

Yes this is a new breed of man who is what I have termed “Low ‘T'”. If you have seen the prescription TV commercials for Low “T”, its all about low testosterone. Now I’m not a doctor obviously and have no way of knowing if the men who truly prefer a woman to initiate are actually Low “T”.  But when you think about it, any man who thinks its the woman’s job to give him her phone number and initiate dating is a man who isn’t “getting much” if you know what I mean.

Hence my feelings about this type of guy’s low testosterone levels. Younger men (well not only younger men) are driven by the desire to have s.e.x. That’s no secret. So if a man isn’t doing what he can to find a woman he loves (to have s.e.x with) or a woman for a one night stand, that’s a sure sign of a low s.e.x drive case closed. Or they fear taking a stand or sticking their neck out.

I found this comment on the Plenty of Fish forum about who should initiate – a man or the woman, written by a guy who shares his point of view and experience with it.

“If I am attracted to the woman, I believe it is my responsibility to initiate and plan out the date. I think one of the worst things you can ask a girl after you ask her out and she accepts is “okay, what do you want to do?” This gives the appearance as wishy/washy and not being able to assert control. Wimpy/whiner guys do this because they are afraid to make any kind of judgement call. If I ask, I will assume control and organize the date….after all, I am trying impress here and show a little bit about my personality.

I believe most women would want a guy to act like a man. Have the ability to take control over a situation when it presents itself. Not need her to be a part of every decision making process. And above all, be strong. Maybe I’m wrong. But believing in this philosophy has not let me down yet during the early “getting to know you” stages.”


Now after the first 4-6 dates, things start to balance out as you enter the first phase of relationship. I think you still want to take the initiate slowly, maybe a 1:3 ratio with the man still take on the lion’s share. This way you don’t overwhelm him or invade his territory. Just keep in mind that in many long-term relationships, eventually the wife plans the vast majority of socializing. So as I said, things tend to balance out. But there’s no need to rush it.

Most dating experts agree, things tend to work best when you let the man lead during the initial get to know you phase of dating. You really can’t go wrong by hanging back. And if you do meet one of those guys who thinks you should initiate, oh well. You weren’t going to win them all any way and that’s still a small percentage of men.






Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony, MSN.com, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

4 thoughts on “With Men and Women and Dating, Who Should Initiate?”

  1. I’ve got the phone number of a man who I have an attraction to. I know him a little but rearely see him out. We are both in our early 50s. Is it wrong to text or phone him and ask him out on a date. I would live to know if he feels the same although I’m very nervous of rejection. Can you help me please.

    • Hey Fiona, You can call him to say hello once and ask him out once, hopefully on the same call. But here are two things to keep in mind. 1) Don’t continue to call or ask him out – that’s when you are chasing a man and that does not work. Turns men off or they take advantage of knowing you like them. 2) You’ll get to know what its like to be a man and feel the kind of rejection they face. Be prepared for him to say no or be evasive. If he is evasive or has excuses, drop it before you end up embarrassing yourself. On the other hand he might say yes an be interested. You’ll know if he goes on the first date if he’s into if HE asks you out in the next date. No matter how good a time you had – do not ask him out for date 2 because that starts a pattern that will not bring you happiness. Sometimes a man says yes because he’s curious, flattered or bored with nothing else going on. So, knowing these risks, if that’s what you still want to do – give it a shot.

  2. I can see the value in us women leaning back in the beginning and not initiating dates, but what about opening a general line of communication?

    I know my lab instructor from last Fall was attracted to me and the feeling was mutual. For obvious reasons, however, nothing ever transpired.

    He did start following me on Instagram and he’s been liking my posts more frequently lately. I want to message him to see how he’s been, but I’d never ask him out.

    Is initiating bad in this regard?

    • Hi Joanne – Nothing wrong with being friendly! Sure go ahead and say hello. Just don’t always be the one starting the conversation – that’s when the problems and the chasing begin. It’s better when a man pursues you because then his interest is more clear.

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