What You Should Know Before Sleeping with Him

Women's Dating

What You Should Know Before Sleeping with Him

Nick Slade Nick Slade • 6/15/15

Prying into a man’s personal life can be a risky adventure. Sensitive information is simply on a need-to-know basis. Well, if you are getting close to the point of becoming sexually active with your new man, there are some things you need to know.

What questions are fair game, and which are out of bounds? And how can you bring up the subject without seeming like you can’t wait to get into his pants?

The time to discuss his romantic resume is not when he is reaching up your skirt. That’s an awkward time to shout out, “Wait! Before you go any further, there are a few questions I need to ask you.” Plan ahead so the sex can remain spontaneous and worry-free.

Know the reality of the situation.

A man just needs to know if you’re willing, although a good man will want to know much more. A woman really needs to know the reality of the situation.

She bears the risk of pregnancy, motherhood and incurable disease. She wants to share this bond with someone who could be “The One,” while he may just be looking for the next one.

You can tell a lot about where a man is going by looking at where he’s been. Realistically, you cannot expect a modern man to make any kind of long-term commitment before or even right after his first sexual experience with you. Unless you were introduced through an Amish matchmaking service, the expectations of dating in the 21st century don’t begin with commitment.

But you can look for respect and a common interest in giving things a fair shot at moving toward a real commitment, at least in the short term.

It is absolutely fair to interview your guy to see if he qualifies for the position you want to fill. Yes, there will be a probationary period for both of you to discover if things are moving in the right direction, but you at least want to start out on the same path.

There are some things you need to know in order to make a good decision about accepting him as a sexual partner.

1. “How long was your last relationship?”

How many times has he been in love? If he’s had a lot of dates but no relationships, that’s a red flag regarding both his intentions and his ability to commit.

Three months is not really a relationship. Six months, maybe, if they were living together. What does the overall pattern of his romantic history look like?

A lot of guys had trouble getting things off the ground in high school, and even for a while in college, so consider if he is a young newbie or a wandering wiener.

2. “How many girlfriends have you had?”

You want to ask him how many women he’s slept with, but that’s not really something you need to know — and you might not like the answer. So, you can let him off the hook for now and ask him how many girls, not counting the ones he was only with once or twice, he has been intimate with.

That will put him at ease for now, but later on, in the “medical” portion of the interview, you’re going to ask him if he’s had a lot of one-night stands.


“If he passes with flying colors, ask him if

he wants to take it for a test ride at your place.”

“Why did you break up?”

  • Who dumped whom?
  • Was there an incident?
  • Infidelity?
  • Or did it just fall apart?

If he doesn’t really know the answers, that’s not a good sign. If he blames everything on her, that’s not a good sign either, although it could be true.

3. “Have you ever been unfaithful?”

Make sure he’s on his second glass of wine before you ask this one. Keep your eyes square on his, and pay careful attention to his body language and comfort level.

If the answer is “yes,” let him explain his excuse to you, too. This is no time for anger or judgment. Compliment his honesty. Ask him what he’s learned. Ask him why it would be different this time. You’re both looking for a fresh start here.

4. “Tell me about your relationship.”

Try to find out if he has a good understanding of the meaning of a relationship. Ask him about the things they did together and how often they saw each other.

Did they go on dates, or was it just a series of booty calls? Did they have daytime dates and meet each others’ parents? Were they in love?

5. “Tell me about your ex.”

Find out what kind of girl she was.

  • Was she educated?
  • Did she work?
  • Was she pretty?
  • How long did he know her before they made love?

6. “Do you always practice safe sex?”

Some guys will tell you they just don’t like condoms and won’t use them. Honestly, nobody likes condoms all the time, but these days they are a requirement. There is no reason to let an hour of pleasure change the course of your life, and not in a good way.

You’re only response should be, “Then I guess we’re done here. Goodbye and good luck.” That may change his mind, but it has to remain non-negotiable for at least six months, and he will have to get a medical exam now and again after six months.

Keep in mind that this is really a conversation, not an interview. In fact, it’s a good idea for you to answer some of these questions about yourself first, and then follow up by asking him the same thing about himself.

You’re going to toss out any negative things he says anyway, believing that things will be different with you. But you’re a big girl, so make a decision that works for you.

If he passes with flying colors and you’re sure he’s “clean,” go ahead and toss down one of those new Fire & Ice condoms in front of him and ask him if he wants to take it for a test ride at your place.