Dating Guide

Being a “serial dater” usually means you date around a lot, oftentimes resulting in an overlap where you’re dating a few different people at once. Sometimes being a serial dater has a bad social stigma, but I don’t think there is anything inherently wrong with it from an ethical standpoint. For some people, they’re at a stage in their life where it makes more sense to maintain a couple of casual relationships than one serious one. There’s nothing wrong with that.

The thing about dating a few people at once is that it can be downright tricky. I care a lot about the feelings of the people I date. Even if I’m not particularly interested in them, I place a high priority on their value as an individual and don’t want to do anything to hurt their feelings. That’s where it gets tricky. Here are a few things to keep in mind for dating multiple people at once:

Don’t Mention the Others

I never, ever mention another person that I’m dating to someone that I’m dating. As far as they all know, they’re the only person I go out with. Now, I’m not advocating that you lie. If any of them asked me how many other people I’m dating, I would tell them that I don’t think such a conversation is going to lead to anything productive. If they insist, I’ll be forthright with them and tell the truth.

Dating is about two people enjoying each other’s companionship and making each other feel special. You’re not going to make them feel special if you’re always referencing some other person through which, contextually, you’ve made it clear are more than “just a friend”. Women are particularly horrible about this. C’mon ladies, we don’t want to hear about some other guy when we’re out with you. When on a date, give the person you are on a date with 100% of your affection and attention, and leave it at that.

Take Notes

It sounds a little odd, but I like to jot down notes of people I’m dating. Where they’re from, what they do, a few random items of things they like or funny things that we’ve talked about. After any date, I write down a few notes from the date and tuck it away for later. If I’m going out with that person again, I study the notes for a couple minutes before leaving for the date. It helps keep you in an appropriate frame of mind in which they are receiving you full attention. You don’t need to maintain a ton of complex notes, just a couple of random tidbits should be sufficient for triggering your memory of the person.

Silence Your Phone

I put my phone on “vibrate only” when on a date. I recommend doing this even if you’re only dating one person. It can really kill the other person’s good-vibes or confidence if your phone is constantly making noise during the date. I also make it a point only to check my phone on a date if the person excuses themselves for the restroom, or any other situation arises in which I have a few moments to myself.

Keep Your Bedroom Spotless

If in the event that a date leads to returning to your place, you’ll want your room to be free of any evidence that you’re dating someone else. Before leaving for any date, pick up the condom wrappers, remove the random long strain of blonde hair from the pillow, tidy the place up. I promise nothing will kill the sexual vibe more than having someone discover an empty condom wrapper in your trash can shortly before the two of you were about to start being intimate.