Cleo's Dating Blog

When is the Right Time for Sex?

Posted on: January 19, 2011

Disclaimer: This post is for mature audiences only. I am going to do my best to be straight forward and honest with this subject- although it may be challenging since I am abstinent and waiting until marriage (as of yesterday… maybe, hehe).

A man friend recently requested that I write about what every man wants to know most, which is, “what is the best time to first have sex with a new girl?”

This subject reminds me of a Mike Posner song, Bow Chicka Wow Wow. Here are some of the lyrics:

Are you tryna make me late, wait wait till the second day
But I cant cant cant even contemplate
Waiting one more minute, lemme jump in it
I brought you flowers and a teddy

You’ve been playin naughty, getting with me all night
We both know exactly what you want right
Tell me what you want though
Tell me what you gon’ do…

The song illustrates well the battle between men, women, and sex. First, the female is acting naughty, sexy, flirty and sending signals of wanting to “get down” to the male. Male takes signals literally and buys flowers and teddy to ensure that the deed occurs- simply following a social norm. However, since women are complex beings, it is more likely that the female wants only to be lusted after but does not actually want to engage in the lustful act (at this time), as shown by her wanting to wait in the song. Male can not wait. Thus he is going to keep trying and trying and trying.

So we have a minor dilemma and a compromise is needed. Man may ask, “sex feels good, why would a girl even want to wait?”

First, some preliminary questions?

1. Are you and your female on the same level of attractiveness? Often women give off mixed signals simply for attention, for the fun of it, or to be friendly. I know because sometimes I am guilty of this and I have to ask myself, “wait, what impression is this guy getting? do I really want to rip his clothes off?” More often than not (like 95% of the time) the answer is “NO” and I consequently need to readjust my actions. Ladies, be careful what signals you are sending.

2. Are you a trustworthy person? A semi-experienced gal knows that sex is better if there is some level of trust and emotional connection. If a guy does not seem genuine, his chances of getting laid are much lower (unless alcohol, lavish gifts, etc are involved). Thus a man could ask himself, “what level or amount of effort have I put into courtship?” If the answer is “minimal” than any self-respecting girl would give you minimal amounts of playtime. As a side note, courtship does not equal expensive dinners or long talks on the phone. The easiest yet most important forms of courtship include listening well, paying attention, being thoughtful, texting back in a timely manner, and not being too aggressive. Excessive peer pressure is never necessary.

3. Do your intentions match the type of girl you are going after? I will not be the first to cast a stone at someone with the sole intention of getting laid. Being straight forward with yourself and you sex prey is important. However, if that is your intention, then a classy girl, like Cleo for example, would be the wrong person to go after. Make sure you choose wisely.

Alright, so you are a good match and you like the girl… now what? As a a general rule, i’d say waiting anywhere from 1 week to 1 month is reasonable. Of course it also depends on how often you see each other and when your/her last relationship was. It also helps if you can gauge whether or not she is “seeing” anyone else at the time. Do not be too quick to assume that you are her #1. Sloppy seconds or thirds never feels as good (from what I hear) and a good girl only goes with one at a time. When you start to feel like Mike Posner and that you just can not wait one more moment, bring up the subject to her. Sex is natural and should not be considered taboo. The more often you talk about it in a tasteful manner, the easier and more comfortable it is to bring up in conversation. I personally think it’s fun! hehe

Ladies… how do you know if sex is the right choice? Do you want to wait but sometimes it seems easier to just give in so the guy will stop trying so hard?? Let’s be honest, men can be really annoying. Sadly, that is never a good enough reason to give it up.

Here is what I find to be true:

– Sex without emotions is just as good as sex by myself… and sex by myself is much less risky!

– Sex too early with a guy (thus, without having any real emotions) is not going to be great. It may be fun at the moment, but the next day you will think, “ehh.” My roommate describes the feeling as having an emotional disconnect from yourself. If the sex does not feel right, then I do not feel right. And if I am dating a guy that does not make me feel like myself, then I will want to find another.

– Faking emotions to have good sex is only harmful in the long run. This is when you can become wrongfully attached to a man that in reality, you probably do not even like.

– Pretending the guy is someone else is just rude (oops). And if you are really good at it, this can also lead to wrongful attachment.

– If you lead a man on too much, you become a bitch if you do not properly “take care of” the consequences.

– Good sex is worth the wait… a good man even more so.

Basically, when it comes to deciding what is the right time for sex, you must follow your gut feeling and not any other body part (not even your brain). Your mind can trick you into believing what you want, i.e. “I know he is in love with me,” when it has been two weeks or “he told me he only cheated that one time so I trust him again,” when you know deep down that’s absurd or “she gave me her phone number so I know she wants me,” which is just wrong.

So be smart (and safe) with sex and have fun!! And as always, let me and the readers know what you find to be true.

Love you,


2 Responses to "When is the Right Time for Sex?"

Another thoughtful and complete dissection of a complex matter. Bravo. I’ve learned that spontaneous sex between a friend is 100 times more fun and mutually rewarding than any rushed sex with a new gal I’m starting to date. Thanks for breaching the subject. It’s so healthy for us. You’ve found a writing groove sista.


I think sex is something that shouldn’t be manipulated by a time frame or numerical value, such as “talking a month” “several dates” “[5] sleepovers”, etc. But rather something that just happens by occurrence. Yes it’s good to not be a “slut” and you shouldn’t give yourself up even though you may be feeling “in the mood” to somebody you barely know and whom you’re attracted to. However you can’t set certain criteria or expectations when engaging in the act of sex. It just happens. It should not be set up like in high school, where girls plan on losing their virginities “at prom” if they haven’t already. We’re not kids anymore. I have more to comment on but have to go for now, ciao.

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