7 Questions to Ask Before Sleeping with Him

by Janet Ong Zimmerman on 06/14/2016

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At 29, physical chemistry get the best of me and I found myself in bed with a guy on our second date.  For months after, I cringed every time I thought about that.  You see, I wasn’t the type to just jump into the sack on such short notice.  To understand why that happened, you’d have to know the context.

I was fresh out of a 7 year on-again, off-again relationship of which we stopped having sex 5 years into our relationship.  For 2 years, I had no sex.  So when we finally broke up, my body was longing for that physical connection.

I met him at the gym and on our first date, the conversation flowed.  On our second date, we went dancing and had a lot to drink.  Alcohol made my inhibitions go away and when we went back to his place, that’s when things got steamy.  Sex happened.  Had I been sober and not naive, I may have known to ask these questions and save myself from heartache and pain.

Don’t be naïve like I was.  Learn from my mistakes by asking these questions if you’re thinking of sleeping with a guy you’ve just met.  These questions go both ways; the guy you’re with may also have these questions for you.

1. Is he available or am I a rebound?

It turns out, the guy I slept with was fresh out of a break up with his fiancée.  She was the one who broke things off and he wasn’t available because his heart was still with her.  But I didn’t learn about this until after we had slept together a few times.  And by then, I was infatuated with him.

The lesson here is if you are wanting more than just a hook up, find out if he’s available and wanting something more.

2. Am I inebriated or sober?

If you aren’t the type to just sleep with someone early on when you’re sober, then the after effects of sleeping with a guy when you’re inebriated, is going to be awkward and make you feel uncomfortable.  Liquid courage only lasts for so long and once the morning after arrives, you will tend to feel awkward.

The lesson here is it’s better to decide to sleep with a guy when you’re sober.

3. What is his sexual history?

According to C.Everett Koop, MD. former US Surgeon General, “When you have sex with someone, you are having sex with everyone they have had sex with for the last ten years, and everyone they and their partners have had sex with for the last ten years.”  In the heat of the moment when things are hot and heavy, that’s not something we think about.  And after sex happens, if he has a sexually transmitted disease or infection, you run the risk of getting that too.

The lesson here is to ask about his sexual history and to find out if he has any sexually transmitted diseases or infections.  The reality is, some people aren’t honest about this so to reduce your risk of disease, infection, or pregnancy, it’s always best if he wears a condom.

4. Does he care about more than my body?

It’s flattering when that cute guy compliments you on your appearance.  But if your conversations and texts revolve around physical appearance and are full or sexual innuendos, he is after your body.  If you think there’s a chance that he could be a good guy, use the three strikes rule.  If after the first two times you’ve expressed that sex is something you love sharing with a guy who _____________ (or when you feel __________), and he is continues making sexual innuendos in your third communication, he’s not for you.  The exception is if you’re looking for just sex, then go for it.

The lesson is some guys are used to getting away with sexual innuendos because some women have allowed.  To give a guy the benefit of the doubt, give him three opportunities.  And if he keeps with the sexual innuendos, leave if it bothers you.

5. Do I like who he is?  Is he a good person?

I liked him because he was charismatic, successful in his career, and seemed mature.  At that young age, I didn’t have the wisdom to realize how important integrity is.  One day I met him at his house a month after we were seeing each other and there was a “for sale” sign.  Up until then, there was no indication that he was moving.  That is not a sign of a good person.  To be clear, he was not a good person.  He really was just using me.

The lesson here is to recognize that a good man is honest and upfront about his intentions.

6. Am I sleeping with him because I want to or because I feel pressured?

He said all the right words and had all the right moves so technically he didn’t pressure me.  But his words, moves, and the pressure I put on myself led me into having sex with him.  While he didn’t physically pressure me, the internal pressure of wanting him to like me and wanting to seem cool was the tipping point that landed me in his bed.

The lesson is sometimes it’s not obvious you’re being pressured when a guy is really smooth because he’ll say and do things in a way that makes having sex seem like your idea.

7. Do I want a fling or a potentially lasting connection?

Of course, even if you’ve connected in multiple ways and know each other at a meaningful level, there’s no guarantee that things will work out.  But there are certain things you can know.  In my case, it didn’t occur to me to ask if he was moving because he had just moved to Kansas from Texas.  But a month into things, I found out he was moving to Colorado when I went to his house and saw a “for sale” sign.  I was not prepared for that!  If I’d knew he was just looking for a fling and I was his rebound, I would have saved myself some heartache and not continued sleeping with him.

The lesson is a guy may not always be upfront about his intentions so you’ll want to ask or pay close attention to anything that doesn’t feel right.  If something doesn’t feel right, honor those feelings.

How will things be after we sleep together and am I prepared for that?

In my naiveté, I assumed we were going to turn into a lasting relationship and didn’t even think otherwise.  Because I wasn’t prepared to be someone’s fling and rebound, it hurt immensely to realize that our connection was going nowhere.  While there are no guarantees that any relationship will last, the one guarantee of a promising relationship is the feeling of ease.  During my short time with this guy, anxiety was a central theme.

The lesson is if you’re constantly feeling anxious, the less likely you are to feel good about things after you sleep together.

The takeaway

To be clear, there’s nothing wrong with having sex with a guy early on if that’s what you want.  But from my experience and my clients’ experiences, the aftermath tends to be hard for most women.  We sleep with a guy hoping for things to turn into more, or we try to act like we’re fine with just sex when we really want a more meaningful connection.

The takeaway is asking these questions before having sex.  This lets you see clearly what you’re getting into and whose getting into you which helps reduce the possibility of heartache and pain that can come from the aftermath.

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