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!

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