How to Not Kill Your Chance at a Second Date

– by Wendy Morley, Publisher –

dateNever in the history of time have there been more ways to meet someone, from online to apps, and even (gasp!) the old-fashioned way, meeting people through friends and colleagues.


Back when your grandparents were dating, everyone knew the rules

But while getting a first date might be easier than ever, so is fucking it up. Back in the days when your grandparents were dating, everyone knew the rules: You dressed your best. The man picked up the woman, chose the venue and paid for the date. Everyone knew what was off-topic for conversation, and everyone knew that good girls didn’t kiss on the first date.

These days everything is up in the air. That means more freedom, sure, but it also means some expectations might vary from one person to the next. Be that as it may, some choices are going to pretty much guarantee failure and others will give you a much greater chance of success.



  1. Don’t Be a Bum
Keep your own style, but do make sure you and your clothes are clean

You don’t have to dress up, but do be clean

Whether your style is urban, hipster, sophisticated, artsy or sporty, make sure your clothes are clean and presentable. I once went on a first date wearing a fairly typical first-date outfit: a casual dress and sandals. He, on the other hand, showed up in a threadbare t-shirt, shorts that looked 25 years old and flip-flops. There was no second date.


  1. Show a Little Effort

This is related to #1 but not exactly the same. Ok sure, I don’t want the pressure of feeling like my date spent an entire day prepping, but make a little effort. At least look presentable. If you spend zero effort on getting ready for our date then I’m going to seriously question the effort you might put forth as a potential partner.

A walk with ice cream is way better than a stereotypical coffee date

A walk with ice cream is way better than a stereotypical coffee date

Looks and dress aren’t the only places some effort is valuable. Also the venue and the activity. If someone wants to meet me at a chain coffee or donut shop it doesn’t mean the short-lived relationship is over, but it does take them down a notch or two. A walk down by the waterfront for ice cream is better. Or how about a picnic? Or a street festival? Do you know a really cool spot to watch the sunset? A little creativity goes a long way.


  1. Trying to Impress

Remember the Genie in Alladin before the date with Jasmine? “Beeee yourself,” he said, and you should remember this before any date. The two quickest ways to not impress me are 1) being a jerk to the server and 2) trying to impress

Great, you've got a nice car. I assume I'll see it at some point if we date again

Great, you’ve got a nice car. I assume I’ll see it at some point if we date again

me. You really don’t need to brag about things you’ve accomplished, the car you drive (ugh) or how you were the star on some championship team. These things will all come out over time, but what we need to impress each other with right now is ourselves! Converse, laugh and flirt. If you aren’t genuinely enjoying each other’s company then all the cars and championship rings and accomplishments mean nothing. No, really. If the woman you’re on a date with is so impressed with these things then do you truly even want a second date? Your call.


  1. Talking About Sex
Don't rush the sex talk.

Don’t rush the sex talk.

Hey, if you’re both into hooking up then have at it. And of course sex is important for an ongoing relationship. But if you’re looking for something more to stem from this date then really, save it for mutual discovery. If you start talking to me about sex on the first date then I think that’s all there is to you, and you’ve just slotted yourself as a one-date-only or a FWB at best.


  1. Talking Too Much – or Too Little

In my experience it’s usually too much. He goes on and on while my mind starts to wander. Yes, I understand you’re maybe a little nervous and yes, you maybe talk more when nervous, but try to take a deep breath and hold back a bit. Ask questions. Allow your date to answer, uninterrupted. You can give your perspective later, or if this goes well even on another date! Your life history and your opinions on everything mentioned do not have to spew out of you in one go.

On the other hand, being so shy that your date has to lasso a word out of you will make the evening a struggle instead of a joy. Happy mediums are called happy for a reason.

  1. The Tough Part: Paying
Traditionally the man's duty, the concept of paying has become a bit of a minefield

Traditionally the man’s duty, paying has become a bit of a minefield

Best is to decide this early on, but it is a bit of a tightrope. Lots of guys get irritated by being expected to pay, but just as many get insulted if the woman attempts to pay. It’s pretty much no-win. I personally pay for at least part of the first date. He gets dinner, I get drinks. He gets coffee, I get ice cream. You might have to play it by ear, but I think it’s a good idea to expect to pay no matter which gender you are and not matter what financial state you or your date are in. In other words, if you’re poor and your date’s wealthy then it doesn’t matter. To me this isn’t just a matter of respect, though that’s part of it; it’s also a way to prevent manipulation or misunderstanding. It means I do not feel beholden to him, whether for physical affection or for a second date. I feel terrible if it’s not going anywhere for me but he’s paying. So in that case, I’m almost always the one who grabs the check. Keeping the first date inexpensive is also a good rule to follow.

  1. The Next Tough Part: The Kiss
Watch your date's eyes. If they're on you, the attraction is there. If not, well you might be out of luck

Watch your date’s eyes. If they’re on you, the attraction is there. If not, well you might be out of luck

This is so much a matter of personal decision that it’s really hard to give any advice, but if you do want to have a second date (and then some), then I think it’s best to leave your partner hungry for more.

But how can you tell if your date is as into you as you are into him/her? You might be aching for a kiss whereas your date is just aching to leave. There’s nothing worse than leaning in for a kiss and your date pulling away. Ego stomp.

First, notice where your date is looking throughout evening. Looking at you, looking at your eyes or lips and leaning in are all signs of interest.

Second, touch. Touch his/her arm or hand in a natural way, during conversation or walking, for example, and see what the reaction is. Does your date draw closer or immediately pull away?

Third, touch a little more. Allow your hand to linger on her back when you are getting into a taxi or crossing the street, or lean in a little toward his arm at a cross walk. Again, judge the reaction. If your date is pulling away at either of these points or sitting far away from you in the taxi so your legs can’t possibly touch accidentally, it’s not looking good.

The first kiss should leave you both wanting more

The first kiss should leave you both wanting more

Finally at goodbye, give a very light kiss to the lips. Is your date still touching you? Pulling you closer? Looking at your lips or eyes? If any of these things are true, then you can safely go in for a longer kiss.

The first-date kiss should whet the appetite, making you both anxious for more. I think this is even more the case if you’re a guy. Women are constantly being hit on, and are generally able to get any degree of sex whenever they want. It’s a little disarming to have a man pull back and not try to take things farther, especially when he is so obviously interested. And this, in turn, will help keep her interested.

Oh yeah and the last thing – please, make sure your breath is fresh. Nothing worse than wanting to kiss someone only to find their mouth smells like a sarcophagus.

1 Comment

  • On point 2, I really like dates that don’t involve just sitting in one place. I hate dinner dates, and drinking is fine but don’t overdo it. One really great first date I had took place at an aquarium. Museums are good, so are countryside walks. As there’s always something new to look at, there’s always something new to discuss. Conversation doesn’t dry up so easily.

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