When Should I Have Sex with Him?

The ladies in my 6-Step Find Hope and Find Him telecourse have been talking about S-E-X. This can be a tough topic for women who are dating after 40. They asked me “When should I have sex with him? How do I decide I’m ready? This is such an important conversation. You may think “I’m not even dating yet…who cares!” But the decision may be closer than you think, and I want you to be prepared.

Sex can be a glorious part of a relationship, but when you get intimate too soon, the experience can wreak havoc on your emotional state. It can also mess up an otherwise budding relationship.

I’m all for having fun and enjoying some amazing sexual intimacy. But if you’ve got love on your mind, follow these tips.

Getting this right is about clearly defining the boundary and behavior you will follow under all circumstances. This is key to maintaining your dignity and confidence, not falling for the wrong guy and keeping safe. Here’s some advice:

1. Answer the question “Is he just hot or is he a hubby?”

If you’re looking for your husband or life companion, you have to approach dating with as much maturity and objectivity as you can muster. Muster it, girlfriend, and decide if he’s just charming and makes you tingle or if he has real depth and relationship potential. If he’s all tingle and no substance, I say slow the heck down or even run for the hills. If you have sex with this man, odds are you will fall for him…because that’s what we do. (Look up how oxytocin affects us.)  And then you’re hooked. I’d rather you wait and get hooked after you decide a man is good, kind and interested.

Here is more about the Is He Hot or is He Husband test.

2. Know what you want and need.

Are you looking for frolic with a great orgasm or for a loving, decent man to share your life? Figure it out, define it and then base all your decisions on heading toward your goal. (Just like you do in the other aspects of your life.)

In order for you to remain safe emotionally, spiritually and physically, you must first set your personal rules and boundaries. Ask yourself what you need to feel, do, know or experience before you will sleep with him. Note that this isn’t about what HE must do…it’s about how YOU will take care of yourself. Here are some examples:

I will not sleep with a man until…
we are in a committed, monogamous relationship.
I get his promise that he will wear protection and take care of that part of our relationship.
I know his personal information. [Define what that is.]
I feel like I trust him enough to be comfortable naked with him.
He knows about my [anything you think he should know before you’re intimate].

3. If you can’t talk about it, don’t do it!

Once you know what you need, and before you sleep with him, be sure that the two of you are on the same page. Too many times I’ve coached women who thought they were in an exclusive relationship only to find out that the man never felt that way. This happens when she assumes…but never had a grownup, open conversation about their feelings, expectations and promises. You don’t want to be surprised this way!

Look, you’re not 18 anymore and you are about to share your body and soul with a man. It is reasonable to want certain things to take place before you make this decision. Are you both committed to exclusivity? Does he see a possibility for a future together? Will he promise to respect your needs around safe sex? Is he understanding about your need to keep the lights off, about your discomfort with your scar…?

Don’t guess these, sister; you have to have the talk and hear it straight from him. And it doesn’t have to be heavy and scary. You can make it fun. This is just part of getting to know one another and developing your intimacy.

Bottom line: if you can’t sit down, look each other in the eye, and have an adult conversation about your relationship and safe sex…do NOT have sex with him!

4. Don’t drink.

There’s a lot of emotion and body chemistry flying around when you two are in the ‘let’s hop in bed’ mode. Do everything you can to keep your wits about you. Alcohol is actually a stimulant and doesn’t make you more charming. (Except to another drunk person.) If you must, savor one or two nice glasses of wine. But until you decide it’s a good time to be intimate, lay off the booze.

5. Follow the Dalai Lama.

In his book The Art of Happiness: A Handbook for Living, the Dalai Lama talks about pleasure versus happiness. His advice: always ask yourself “Will this bring me happiness?” Pleasure is fleeting…happiness is for life.

I try to follow this in my life in general; it’s a powerful guide to making good decisions. It’s especially handy when you’re considering getting physical with a man. Stop and ask yourself: will this make me feel good AND make me happy? You know from your many experiences that something that feels good now will not necessarily bring you happiness. (C’mon…you know what I’m talking about.)

I’m all for having fun and enjoying some amazing sexual intimacy. But if you’ve got love on your mind, follow these tips. I assure you that they will limit your disappointment and help you find the happiness you so deserve. A good grownup man will go right along with you.

Remember…always be good to yourself and love yourself as much as I do!

  1. Like I said, Isabelle, you have to decide what you need to feel safe and the right man will respect it. Without getting too personal, I don’t know a lot of couples who are doing all that fun sexy stuff on the regular. If the man you’re dating wants this, sounds like you’re not a good match. To love…Bp

  2. Hi Bobby,
    How can I cope with the internal pressure of respecting a man’s need for sex and the fact that I’m slow to get sexually involved? I’m 50. I know I enjoy sex but have not had it for 5 years. My body had changed. I’m still raising my two children age 13 and 14, starting a new career. I’m scared to not be up to par with what I hear is done out there: durty videos, sex talk over the phone, masturbating in front of him, etc. I feel this can be done but much later in a relationship. The man I met passes the prerequisites but has experienced the kind of relationships I described above. I feel pressure to perform in an area that takes me longer to attain.

  3. […] (Btw, if you are wondering about my advice on when to have sex, you can read it here, and here.) […]

  4. Hi Tammy, Before you’re intimate, you want to share your needs with him and be sure he is amenable. The last thing you want is to have sex with a man only to find out after that he doesn’t want a relationship or won’t commit to monogamy, right? So, if you find you’re getting to know him and are headed toward intimacy, have a convo that goes something like this: I’m enjoying my time with you and I’m really attracted to you. Before we are intimate there are some things I’d like you to know about me…or I’d love to hop in the sack with you but there are some things that would need to take place first. Talk to him about what you need. Do you first need exclusivity/a promise of monogamy? Do you want STD testing and/or to practice safe sex? These are things to talk about first. If he’s a grownup like you are, he will welcome the discussion. Hugs, Bp

  5. Can you give an example of what the “sex” talk looks like when you’re newly dating at 50?

  6. The protocols and practices of dating, and the terms used to describe it, vary considerably from country to country. The most common idea is two people trying out a relationship and exploring whether they’re compatible by going out together in public as a couple, who may or may not yet be having sexual relations. This period of courtship is sometimes seen as a precursor to engagement or marriage.;’

    Have a good day
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  7. Thank you for this article. I have slept with a guy just because I thought he was hot and it never went anywhere. I have learned to put on the brakes and wait.

  8. Hi Kara! You know that I’m truly grateful to have the opportunity to contribute positively to your life. I admire your willingness to share so honestly and learn new things. I hope you know that you’ve become a great source of support to the other women in our Meetup Group. Keep up the great work…hope to see you at this month’s meeting. Big hug to you.

  9. Hi Bethany: First let me say how brave I think you are to make such bold steps to move forward after your losses. I’m glad that you’re focusing on creating a fulfilled life for yourself, and I agree that meeting a man while you live your fabulous life is the best way to go. A happy and interesting woman is a man magnet to be sure. However, getting “gussied up” has as much to do with you feeling attractive and good about yourself as it does about attracting men. When you feel pretty and feminine, that comes through. Now I know you’re not going out in your running suit with your hair in a bun, but I do encourage you to be conscious of how you dress and feel any time you venture out. You never know when he’s going to cross your path! And speaking of that, I do believe that you attract what you truly want, but you also have to put yourself in situations where you can be found. That’s not to say you have to go to single’s events or jump online. But looking for opportunities for socializing that include the possibility of including available men is a good way to go.Have some nice times, and I know you’ll find what you’re looking for. Thanks so much for stopping by and leaving your note.

  10. I Just wanted to say how much I enjoy the things your write Bobbi and you always bring great insight in my life. Thank you 🙂

  11. I’ve been a widow for almost four years now. My stepson moved to another state for college. My two 4 legged buddies said goodbye also through passing. I moved to another state, which is proving to be a wonderful start. Still in my 50’s I am retired also. I’m doing things I’ve always wanted to do and enjoy and love my surroundings. I’m ready to enjoy another man’s companionship and have been told that I should get gussied up and go out. I love to entertain and I love to go to events that interest me. I feel that if the right man comes into my life AS I live my life…it will. NOT because I got gussied up and attended events or social settings where the men are.

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