I would strongly advocate for holding out on the first date. Sex is fantastic but it is not the most important part of a relationship. You should get to know this person in other ways and let the sexual suspense build. If you are looking for a relationship that will last more than one night it is better to wait as long as possible. It will make the sex more worthwhile and feel more meaningful.
Sleeping with someone on the first date gives an impression. It could be the wrong impression. It depends if you want to come across as a slut or not. The person on your other end will assume you have sex with everyone on the first date. That might not be what you want them to think. Anything worthwhile is worth waiting for. It’s important to have willpower and set boundaries if you do not want to be mistaken for a whore.
There’s nothing wrong with being a whore. It’s a lot of fun and it is easier than building a healthy long-term relationship. You can sleep with lots of people (simultaneously or otherwise) and not worry about stuff like “feelings” or “baggage.” The only time I’d advise against it is when trying to find a life partner. You want this person to know you for who you are on the inside, not who you are …on the inside.
You want to know what type of music this person likes… their favorite color… their favorite super-hero… and then find out what their favorite position is. If you jump to the sex than there won’t be anything to talk about afterwards. A sexually-charged relationship is great but more often than not it leads to a sexual relationship and nothing more. You will have a great month or two and then try to figure out what you have in common. Hopefully you both like mini-golf… otherwise it will be very hard to make it last.
I’m not saying it’s impossible to have a great relationship with someone if you have sex on the first date. It is not impossible. It can be done. I’m suggesting that you hold back for a while and tease each other. All relationships take hard work and patience. Getting to know someone is a large part of what makes the courtship exciting. Take your time exploring each other. Just hold off on the sex. At least for a few dates. It will make you feel like naughty teenagers. If you want the full effect bring popcorn and Cruel Intentions.
– John Powers