Dating sex questions from a midlife dating freshman to a senior

My neighbor is just starting dating after a 30-year absence. Two weeks ago she joined a service that matches her and men with comparable intellect, education, income and personality. She’s had dates with three men. She had questions for me — many questions!

Frosh: “You have been dating a lot longer than I have. I’m a freshman and you’re a senior. Tell me the rules.”

DG: “There really are no rules. You decide what works for you. You make the rules.”

Frosh: “There have to be rules.”

The RulesDG: “There is the book, The Rules.”

Frosh: “Yes, but it doesn’t cover what I need. I want to know other rules.”

DG: “About what?”

Frosh: “Should you kiss on the first date?”

DG: “Kiss if you want to. If you don’t, and he’s coming in for a lip lock, turn your head so he busses your cheek. When I hear myself think, ‘I want to kiss him,’ it’s a good sign. Sometimes I get kissed by guys without my thinking this, and it can still be good. But it’s better if I know I want to kiss him.”

Frosh: “When do you have sex?”

DG: “When it feels like the right time for both of you.”

Frosh: “On the first date?”

DG: “If you want. I don’t. In fact, studies show that most men don’t consider a woman a long-term relationship prospect if they sleep together on the first date. Although few turn down the opportunity if she’s willing.”

Frosh: “See, that’s a rule!”

DG: “If you want to make it one. Rule 1: No first-date sex. Unless you both just want a one-night stand.”

Frosh: “What if a man wants to progress faster than you do?”

DG: “You tell him you’re not ready. In fact, that’s a great phrase I didn’t learn for a while: ‘I’m not ready to go there.’ It works great to slow things down.”

Frosh: “So what if he wants to go to second or third base and you’re not ready?”

DG: “You tell him so, while removing his hand and putting it where you are comfortable. If he persists, extricate yourself. ‘I’m not feeling comfortable so I’m going home.’ Or if he’s at your place, ‘I’ve enjoyed our time together, but it’s time for you to go now.’ Be pleasant but firm.”

Frosh: “I’ve heard there’s a rule for how many dates before you have sex.”

DG: “There’s not really a rule. Some people say guys have a 3-date rule. If they don’t have sex by the third date, they bail. Greg BehrendtHowever, during the Greg Behrendt show I was on, he said he has a 10-date rule. He thinks people fall into bed too quickly, and they should wait for 10 dates to see if they are compatible enough to have sex. It’s different for everyone, but it is good to talk about it early and see what his expectation is. You may not be ready by the third date. That’s okay. If he’s not willing to wait ’til you’re ready, he’s not for you.”

Frosh: “Women all have different sexual satisfaction needs. Do guys know that?”

DG: “Some do. Some don’t. If he’s only been with one woman for 20 or 30 years he learned, I hope, how to satisfy her. Some think that they will try the same techniques with you and seem flummoxed when they don’t create the same results. You need to gently teach him by telling him you like what he’s doing and ask for what you want. If he doesn’t comply or forgets next time, he’s not interested in pleasing you enough to pay attention. Not a good sign.”

Frosh: “So what you’re really saying is I get to make up the rules?”

DG: “Exactly. Women hold the power to progress or not. Yes, a guy can pull the plug at any time, but it is the woman who decides when it is okay to move forward. So you need to be present to what you want and how you’re feeling.”

Frosh: “That’s a rule I would have never known. I thought the guys had the power. I need to think through what I want, and if something is uncomfortable I need to say something. That is very empowering! Thanks!”

DG: “You’re very welcome. I had to learn all this these past two years, so am glad to pass on some of what I’ve gleaned.”

Got a question for me? Just write it in a comment.

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5 responses to “Dating sex questions from a midlife dating freshman to a senior”

  1. Liz Avatar

    I think it’s very sad that a grown woman has to ask permission to be in control of her own sexuality–her own body. What a statement about our society!

  2. Dating Goddess Avatar

    Hi Liz:

    I don’t think she is asking permission. Sorry if my writing implied that. She’s a very smart, accomplished woman. She wanted to know what the expectations were so she could create a strategy in advance on how to deal with them.

  3. Liz Avatar

    Question: “So what if he wants to go to second or third base and you’re not ready?”

    Answer: OBVIOUSLY you don’t do anything you don’t want to do. If he has different expections and pressures or coerces you, there is a word for that: RAPE!

  4. mary Avatar

    My 17 year old daughter and her friends are well aware of their generations dating rules. That doesn’t mean they do anything they don’t want to, but by generational consenses there is a body of expectations. For example, oral sex is not really sex to her generation and if a couple have been together for three monthes or more there will be some expectation that the girl will go down on the boy (I think her generation is very sexist in that this not usually a reciprocal interaction). After six monthes usually they will have had intercourse. I am not placing a value judgement on this “rule” and these young women are quite in control, they dump any guy who gives them grief. but they know the cultural context of their dating world. Middle aged women reentering the dating scene often don’t have a group of dating friends to guide them. I think this is what the freshman is asking for.

  5. Liz Avatar

    Mary, so you see this as a question about what is normal for a certain age range in today’s dating scene? That makes sense, but I still find it puzzling that a woman would call these rules as if by her mature age she wouldn’t start setting her own rules–without being told it’s ok to do so.