How much is too much initiative in dating?

Karen writes: “I am afraid I am too assertive. I start taking the lead when the man won’t or doesn’t. I see simple solutions (where and when to meet) and make suggestions. Is this really a bad thing?”

DG responds: If you are a dominatrix, you have stuck gold by finding many submissive men!

Not that there’s anything wrong with that if that’s what your into. I have now learned that “goddess” is a very popular term in the dom/sub world — but unfortunately that’s not what floats my boat. But I’ve had many, many men assume this is the case and have eagerly sought me out — but not too eagerly as that would mean they weren’t a sub!

But it doesn’t sound like that’s what you want. I have experienced your situation as well. If you want an assertive man, not a passive one, then yes, your initiating will be a problem. I found in my marriage I did 95% of the initiating of anything and it got tiresome.

So now in dating, when a man flirts, he has to initiate: “Shall we get together.” To which I’ve learned to respond, “I’d like that very much.” If he does nothing from that, I know he’s not that interested. If he says, “Great. Shall we have lunch or coffee?” I say, “I’d prefer coffee.” He has to suggest dates, times, places. I don’t want to sound evasive — in fact I want to sound encouraging! If I have to initiate closing the deal, I know he’s not very demonstrative (and I need a strong man or I’ll run all over him and be frustrated) and I let him go.

Karen: Do I offer to pay/split or not?

DG: Generally, men like to show they are a good provider, especially midlife men, and they will want to pick up the check, sometimes even if they have no interest in seeing you again.

This is one of the reasons I agree to only coffee for the first date. If we are ordering at the same time (meaning he didn’t get there first and order his while waiting for me), I always reach for my wallet. Ninety-five percent of the time, the man will say, “I’ve got this,” to which I smile and say, “Thank you.” If he’s already ordered, he will typically say, “What can I get you?” He’s being the host.

If we’d hit it off really well on the phone and I’m seduced into lunch with him for the first encounter (NEVER DINNER!!!), when the check comes, I again reach for my wallet. I’ll usually say, “How would you like to handle this?” Nearly all the time he’ll say, “I’ve got it.” If he says, “Let’s split it” it means he isn’t attracted to you. No problem. Pay up and be on your way. Don’t look for a kiss goodbye!

I’ve learned men like — really like — that you offered, but didn’t insist on splitting it. They feel emasculated if you insist when they’ve offered to treat. They get a little thrill out of treating; it makes them feel more manly. Don’t steal that from them by insisting on splitting the check.

After you’ve gone out a few times, then you can offer to take him to your favorite place, cook for him, pack a picnic, etc.

(Warning: I’ve learned many men interpret an invitation to your house as really an invitation for sex. One man showed up with his shaving kit on our second date when I’d invited him for dinner! If you’re not ready for that to happen, don’t invite him to your house — even for lunch! Or make sure there’s another couple and they agree to not leave until he has. Maybe I’ve just had too many who make this assumption, but now I don’t invite men to my house for a while. And there are definitely no sleep overs until I’ve visited his home at least once.)

Karen: Do I offer to drive to where he is or meet 1/2 way?  I often date outside my small town.

DG: If he’s interested, he’ll offer to make the drive to you. However, he may accept your offer to meet him half way. Don’t offer to drive to his city/town. If he says, “Let me know when you’re in my town” he has no interest in you, unless he has no car.

Men like to take care of women and doing the bulk of the driving is one way of doing that. However, if you’re an hour away he will appreciate your even offering to split the driving chore. On subsequent dates, you may offer to take turns, but let him drive to you (or meet half way) for the first few encounters.

Karen: I really have a problem with not sharing the burden of dating.  I’ll work on it.

When you realize men perceive this as taking something away from them, it gets easier to accept their overtures. They like to “win you over” and woo you. Let them!

Read “Are you open to receiving.”


Want to know more about how midlife men think? Then download your copy of Embracing Midlife Men: Insights Into Curious Behaviors.



7 responses to “How much is too much initiative in dating?”

  1. Richard Avatar

    Regarding being assertive:

    If I want to take you out on a date, you won’t have a problem with me not being assertive enough. I may be at a loss on what to do, so giving me some hints would be nice.

    “I see simple solutions (where and when to meet) and make suggestions. ” – There is a difference between taking the lead, and making suggestions. Saying “Let’s meet for dinner downtown” is different from “I’ll be downtown for work tomorrow afternoon”.

    I’m not sure how I would respond if the lady were assertive. Usually there would be a reason why I was not taking the lead (probably not that interested in her). If she were assertive, and I really liked her, then I probably would think “great”, rather than be offended. Now, if the problem is he never suggests the Ballet (or the crafting expo coming to town next weekend), then that might be a different problem.

    Regarding offering to pay/split:

    I expect to pay, and I don’t mind paying. However, I am not going to get into an argument. I will take the check when it comes, or give money to the cashier. She may offer to pay for whatever reason. I will say “I have it”. If she comes back again, then I offer to pay my share. After that, I am not going to keep fighting unless I get the sense that she is just being polite. I feel akward when she pays, even if it is a minor amount.

    “They get a little thrill out of treating; it makes them feel more manly.” – Never thought of it that way. I view it as the gentleman thing to do. It is what I am suppose to do. Not so much “manly” as “polite”.

    Regarding driving 1/2 way:

    It is another selfish thing. She may need to leave by Midnight to be awake enough to drive home. Otherwise, she may be willing to stay up until 2am, knowing that her bed is only a few minutes away.

    Regarding “I really have a problem with not sharing the burden of dating.”

    As long as you show interest, and do your feminine stuff, I’m a happy guy.

  2. NKAF Avatar

    This is really great advice! I think it’s important for women to remain assertive while at the same time being careful not to step on the man’s toes when he is trying to be a gentleman. I like the idea of doing coffee/lunch on the first date as well. It’s less pressure than dinner, and definitely less of a time commitment if things go sour. Great blog! Keep the posts coming!

  3. Almita Avatar

    I have had several men tell me that I “just don’t give off vibes.” That is, they had been interested in me romantically at one point, but they hadn’t felt that I had been interested in them. Of course, they tell me this long after there was any chance for us to connect and when they are dating someone else. Because of this, I now tend to compensate (overcompensate?) for my “lack of vibes” by being more aggressive in asking men out myself. I figure, then, there isn’t any question about my interest! I have had a few relationships develop this way.

  4. Mark Avatar

    I think your advice is sound, DG, but all I can say is it’s way too much thinking. Women clearly think about these things a lot more than men do.

  5. Ronnie Ann Ryan - The Dating Coach Avatar

    DG – Fabulous post and one of my favorite dating topics as a coach for women who are single or divorced and dating over 40. In essence, you are describing how to use feminine energy in the dating world so you can appeal to a man’s masculinity. This can be difficult for the “Type A” professional woman. But you have got this down!

    One place I differ a little is in regards to paying the first time. Coffee – good idea because its low cost. However, I recommend not offering to pay and I have 10 Good Reasons Why a Woman Should Never Pay (or even offer) on the first date.

    Sadly, some men are a bit confused about dating protocol. So, when a woman offers, some brush away the offer no problem. Others wonder – if that mean you didn’t like him. Men know that when they are being rejected, a woman often offers to pay her half so she can be done with him.

    That’s why I tell my dating coaching clients not to risk sending him mixed signals. If he can’t afford coffee or is offended that you didn’t offer to share that low cost date, you do not need him. Get past the first date. Then if you want to offer by moving for your wallet – OK.

  6. Randy Sloan Avatar

    As a man back out in the dating game, I can totally agree and say that when it comes to paying for the meal, drinks, whatever… I ALWAYS prefer to pay, even if I don’t see a future for a second date. Just call me old school I guess. (I’m 51)

  7. Richard Avatar

    > I have had several men tell me that I “just don’t give off vibes.”

    I figure if a woman continues to go out on dates with me, then she is interested. If you are interested, but have to decline two or more date requests, then suggest alternatives that work for you. Then I don’t misinterpret your declines as lack of interest.

    Whether there is chemistry is a different issue.