A 3-step guide to eradicate dating indecision

Wondering if you should go on a first date? A second, or third? Here's how to tell when to proceed and when to throw in the towel.

Internet Culture

Published Jan 25, 2013   Updated Jun 2, 2021, 2:46 am CDT

Beth Cook is a dating coach and throws private dating events for San Francisco’s most awesome and unattached. She also writes and draws about her own dating experiences. Want advice? Have advice? Send her an email.

Decisions, decisions. There are so many when it comes to dating! Who should I go out with? When? Where should we go? What if it’s a disaster? How do I know that I am into him/her? It can be debilitating. Girls turn to their friends or silly magazines for answers; guys turn to YouTube or marijuana. Nothing gets clearer.

Much of the confusion circles around how much time one should invest in a certain person. How many chances does someone deserve to win your heart…one, two, or three? What’s the happy medium between giving someone too many chances and calling it quits prematurely?

Today I’m going tackle this popular question: “When should I go on a first, second, and third date with someone?”


If you’ve met someone IRL that you are at all considering dating, go out with that person—immediately (within a week). You already have way more information than online daters have (like the fact that spit doesn’t spray from his mouth when he talks). Give it a try.

Meeting someone online is a whole different story, though a simple one, if you ask me. If someone sends you a thoughtful message, you find their profile even sort of interesting, and their pics kinda cute—all that equals one date. Remember, you can’t deduce much from an online profile. So you should investigate anyone with even a smidgen of potential, for at least the time it takes to drink one drink.


Questions to ask yourself after a first date to determine the necessity of a second:

1. Is this person a decent human being (i.e. seems to have their life in order; is nice to wait staff)?

2. Is this person red flag-free so far (i.e. he doesn’t hate his mother; she isn’t sniffing cocaine in the bathroom)?

3. Can I imagine kissing this person?

If you answered ‘yes’ to all of the above, then you should go on a second date. What do you have to lose? Two hours of your life, that’s all. It’s worth the gamble, and people start showing their true colors on second dates. You might see something brilliant, or appalling.


If you left the second date smiling (instead of wishing you had spent the night curled up on your couch watching Homeland), you should pursue a third date. Presumably you’re happy because the second date conversation flowed smoothly, the vibe was flirty and fun, and the kiss had sparks. Yay!

If you didn’t kiss on the second date, ask yourself “Why the hell not?” and, “Is there chemistry between us?” You’ve just got to have those feelings of romantic and sexual attraction towards another person—it’s crucial. Without chemistry, you’re just friends, and I’m sure you’ve got plenty of those already.

But as well all know, not all dates move clearly through these three stages. What if you find someone pretty cute, but the kissing isn’t great? You poor dear. If you’re anything like me, you’re probably thinking that you can train that someone to do better. Oh, but you can’t. I’ve tried. Many times. [Cue sad trombones here.] Good kissing is the backbone of chemistry.

A friend of mine instills a chemistry clause into the second date, which I think is totally appropriate. If there ain’t chemistry at Date 2, it ain’t gonna appear any later. No third date necessary.

If you think there is chemistry and you don’t have a kiss as evidence to back it up, give this tryst one more chance.

Once you’ve made it to a good third date, it’s relatively smooth sailing. I’ve found most third dates turn into six or nine or twelve dates…and sometimes, even a relationship.

So take a breath, count to three, and dive in.

Photo by InaFrenzy

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*First Published: Jan 25, 2013, 11:00 am CST