• “If you sleep with a man right away, he thinks you’re too easy and doesn’t call you again. If you turn him down, then he feels rejected and doesn’t call. You can’t win either way.”

• “Once you have sex with a man his ardor starts to cool. He starts to lose interest because the challenge to seduce is over.”

One of the most popular questions I get is if there’s a right time to have sex with men that ensures you won’t get hurt. My initial reaction is, “What’s wrong with just expressing your sexuality, even initiating it?” Isn’t it joyous and self-empowering to express your desire and passion when you feel like it? Why should we fight the dopamine, norepinephrine, and phenylethylamine that’s soaring through our bodies and creating that delicious euphoria? Why shouldn’t we just enjoy one of the few free pleasures that life offers us?

As women, aren’t we more financially and sexually independent now than we’ve ever been before? Isn’t that what the feminist sexual revolution was all about? To do what we want with our bodies? Why should we forfeit the accomplishments and hard-won rewards that women have fought so hard for?

But then I pause and think of my recent session with Josie.

Josie, an attractive, confident woman from New York City who was fresh out of a divorce, went to a trendy nightclub one evening with a girlfriend. At the club, Josie met Rick, a business man with Hollywood looks, who immediately asked to buy her a drink. Their discussion moved quickly from their jobs to their spouses. Although Josie was having a great time with Rick, she left early because she had to get up for an early business meeting the next morning.

Rick called a few days later and asked her out. He impressed her by taking her to a hit Broadway show, followed by drinks at a club that had just opened. Josie was very attracted to Rick, and because he spent so much money on the date, she assumed he reciprocated her feelings. She asked him up to her apartment, and before she knew it they were in her bedroom tearing one anothers’ clothes off.

Josie woke up the next morning with stars in her eyes. She fixed breakfast for Rick, and after polishing off the omelet, orange juice, and biscuits she had made for him, he kissed her lightly on the lips, and as he was walking out the door, causally said, “Thanks, I had a great time.”

After he left, needless to say, Josie never heard from him again.

It took Josie three months to recover from feeling humiliated and used from her experience with Rick. She decided the pleasure wasn’t worth all the grief for having sex with a man she barely knew regardless of how “hot” the guy was.

Thinking It Through
Now is a good time to dig deep into your psyche and ask yourself why you want to sexualize your relationship with this man. It’s always good to take a moment to reflect and process your feelings before impulsively jumping into a sexual situation.

You can start out by trying to determine what kind of man you’re dealing with. This could be done by analyzing a man’s “risk factor,” which will help you to reduce your chances of having a bad experience like Josie’s.

Although you can never predict what a person’s going to do, there are obvious red flags you must be mindful of. So, be alert and be honest with yourself when you are trying to determine a man’s motives and/or character. It’s good to think positively, but in this case a little skepticism and a touch of paranoia might be healthy in trying to protect yourself from getting hurt. Sometimes your instincts can tell you if a man is dangerous and a user. Don’t be afraid to go by your gut!

If a guy has a high risk factor, he will most likely demonstrate one or more of the following personality characteristics:

• He’s unreliable
• He has lied to you at least once
• He’s not punctual
• He’s mysterious
• He’s elusive
• He calls inconsistently
• He’s emotionally and/or physically unavailable
• He acts ambivalent
• What he says doesn’t always coincide with his actions

If a guy has a low risk factor, he will most likely demonstrate one or more of the following personality characteristics:

• He’s very present
• He’s consistent
• He calls often
• He’s available
• He’s punctual
• He’s trustworthy
• His actions match what he tells you

Now that you’ve determined he’s a man you want to have sex with, here are some very important issues to think about.

Casual Sex or a Deep Attachment?

After all, we are all sexual beings and there are times we may experience “sexual hunger.” So, if he turns you on and you just want to have casual sex, then go for it, girlfriend! But you must accept that this is what it will be and nothing more. If something comes of it, then so be it. But if not, you got your needs met and you wont feel “played.” Just remember that gratifying your sexual needs doesn’t necessarily guarantee that you’re fulfilling your emotional needs. Also, keep in mind that when you have sex the hormone oxytocin is released in your brain, which will make you feel more attached to him and could intensify your casual feelings, so be careful.

If you want to have sex with a man because you feel deeply attracted to him, possibly in love him, and you want a long-term relationship, you may need to have higher standards and wait awhile longer when evaluating whether or not he’s a keeper. To lower your chances of getting hurt, it’s also important to make sure that he reciprocates your feelings.

Don’t Use Sex as an Escape Route

Using sex as an excuse to run away from your problems may not be the greatest reason to sleep with a man. You’re better off trying to work through whatever you’re struggling with than using sex as a method of escape. Although sex feels good, you’ll be right back to your problems when it’s over, with possibly more problems because you’re now attached to someone who may not be a good choice for you in the long run.

Prepare Yourself for Anxiety

When you have sex with a man, you’re taking a big emotional risk, so it’s natural that you may feel anxious afterward when you both have to separate and carry on with your daily lives. The unknown is scary after you’ve taken a big emotional risk, so have friends ready to talk to and activities to do (including work) to keep your mind occupied.

Take Care of Yourself Physically

You can’t completely protect yourself emotionally, but you can protect yourself physically by using condoms. The percentage of women getting HIV from heterosexual sex is rising. Don’t think you’re invulnerable. Don’t be in denial. Having unprotected sex is like playing Russian roulette.

Consider Setting Boundaries and Limits

When you’re in a sexual situation with a man, know you can stop whenever you want to. This may sound high schoolish, but you don’t have to go all the way! You can still be sexual without having intercourse. Perhaps this compromise will help you be more comfortable until you feel ready.

Be Honest

There’s nothing wrong with being honest and upfront with a man. Own your truth. Tell him what the deal is before you have sex so there are no misunderstandings later on. For instance, if you know that you are looking for a boyfriend and not a fling, you can tell him that you are not into casual sex, and if that’s what he’s interested in then it’s probably not a good idea for the two of you to hook up. You also have the right to ask him what you need to know to help you make the best choice. For instance, you can ask him if he’s seeing anyone else, what he wants from hooking up with you, or if he’s looking for a relationship. Listen carefully to what he tells you. If he’s honest enough to admit there’s no future and it’s just for the night, then believe him. Don’t play mind games with yourself. Don’t be grandiose and think that you’re the exception. See how he reacts to what you tell him. After you hear what he comes back with, evaluate whether or not he can meet your needs and then make your final decision.

*Warning*

When you’re trying to determine whether it’s emotionally or physically safe to have sex with a man, don’t drink or take any drugs. You want to be alert and have a clear mind. If you want to be smart and make the healthiest choices, you don’t want anything in your system that will cloud your perception.

After Sex

After you’ve had sex with a man for the first time, be yourself but hold back a little. Take your cue from how he responds. If you’re lucky enough to have sex with a great guy who’s telling you how happy he is to be finally hooking up with you and calls you the next day, lucky you! Just enjoy the process. You don’t need to read any further.

However, if he acts cold and detached or wants to leave without even cuddling, don’t cling to his ankles as he walks out the door. I strongly advise against making a scene. Wait till he leaves, and then you can get crazy and call all your girlfriends. If it makes you feel a little better, you could say something about his distancing behavior, but make sure you sound calm. A little constructive criticism probably won’t hurt him. He may need some coaching in this area. Just don’t come off as verbally castrating or reprimanding. Remember not to give him the satisfaction of how upset you are. Work out your deep feelings with people in your support system.

If you don’t hear from him again it could be for a number of reasons: he’s scared of a relationship, he has a girlfriend, he’s married, he just wanted a one-night stand, or he’s having an anxiety attack.

If you are looking for a relationship, I don’t suggest calling him. If you don’t hear from him within a week, he’s just not good relationship material, no matter how amazing you thought he was. Instead, grieve and mourn the loss of him and the hope of the possibilities of what you both would have had together. Chalk it up to experience to learn and grow from. Hopefully, the sex was good.

If casual sex is your goal and nothing traumatic happened, you could say something like, “I had a great time, let’s do it again.” Only suggest this if you can emotionally handle risking his not responding favorably.

No matter how things pan out in either case, remember you are not a victim; you had a choice. Take it like the great woman you are.

So, when is the right time to have sex with a man?
I think anywhere from two dates until two months is a reasonable amount of time to wait to have sex with a man. Whether it’s the first date or two months later is individual. It depends on your comfort level. Although I don’t think it’s a good idea to have sex when you’re not ready just to please a man, I also think it’s not a good idea to purposely put off sex just to see how long a man will wait. Either having sex to “get” the guy or not having sex to “test” the guy is manipulative and an expression of a woman’s own psychological issues, which is not based on an authentic intimacy and relationship. The sad truth is that most men in the American culture who are capable of a relationship, who you and other women find sexually attractive, will probably have a difficult time waiting longer than three months. So if you’re going to make him wait four months to see if he really cares, his feelings of frustration, deprivation, and rejection will probably cause him to leave you anyway. The nicest guy can feel insulted even though your reason to wait has nothing to do with his desirability. If you explain that you need to wait because of being hurt by men from your past, don’t expect a man to be so generous and take the hit for your past insensitive boyfriends; it’s just not unrealistic. The only men who could tolerate waiting four months or longer are probably gay, sexually dysfunctional, or afraid of intimacy, or they just enjoy being with woman who are frustrating or withholding.

If a woman needs to make a man wait longer than three months, she may be struggling with her own sexual issues. I think she should look into why it takes her so long to feel comfortable having sex with a man. Is she distrustful of men? Did a man hurt her?

Here’s a list of the pros and cons of waiting to have sex with a man to help you determine when the best time is for you.

Cons of Waiting

Waiting at least three to five dates until two months is reasonable. But if you wait and he still leaves after you become sexual, it will be even more devastating because you’re more attached to him.

• By having sex with him you get to know him in an intimate way that will help you to determine if you want to keep seeing him.
• If it’s meant to be, it’ll work out no matter when you have sex, so why bother waiting.
• Be true to yourself, and if you’re really into him then go for it—why put up pretenses?
• It feels good to make love, connect to a man, and have intimacy.
• If he’s going to abandon you after sex, you might as well sleep with him, have a good time, and just get it over with.
• Enjoy your life! We only have a short time on this earth—who knows what’ll happen tomorrow.
• It will accelerate the relationship and intensify the bonding.

Pros for Waiting

• The sex could be better when you finally do get together because you have the foundation of a relationship, which can intensify the passion.
• You get to know the man better, increasing your chances of predicting what he’s going to do.
• It gives you more of an emotionally healthy relationship to fall back on if you encounter relationship problems—it’s not a relationship that’s based on sex.
• The sex could be better because you built up sexual tension.
• You never know when a man can throw out that you had sex too soon or accuse you of being promiscuous.
• It gives you more time to see if he is being honest about seeing you exclusively.
• If the relationship ends, you can never blame it on having sex too quickly.
• You’ll feel more comfortable, and the sex will feel less awkward.

Trust Your Own Judgment

No matter how you play it, there are no formulas or guarantees about how things will turn out. There are women who have sex with men the first night they meet and they wind up marrying them. There are women who have sex with men right away and get dumped by them. Still other women wait months and months and only to get hurt or rejected. Having sex with a man you’re first getting to know is always a risk. But be a smart gambler, trust your own judgment, and try to accurately calculate the odds. And enjoy life; indulge yourself in pleasure, while still protecting yourself both emotionally and physically.

The Dating Cure articles are supplied by psychotherapist and author Rhonda Findling. Her website is http://www.rhondafindling.com