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How much is too much initiative in dating?

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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.


About Yury Zvyagolskiy

Yury Zvyagolskiy
In almost all American movies there is a bad guy who is usually Russian and his name is Yury. If the bad guy is not from Russia, his last name usually starts with Z. So here I am - Yury Z. My specialty is personal effectiveness. I am an expert in goal achievement, personal effectiveness, relationships and effective thinking.

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