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The Art of The Successful First Date – Even If She’s Not ‘The One’

How to have a great first date How to have a great first date

Note from Alex: This is a guest post from a woman. Her name is Nicola Lees, and she has been so kind to write about first dates and what to do (and don’t do!) on those. She gives some advice you can’t go too wrong on, so I’ll lend the word to Nicola…

As a single woman in London, I’ve been on a few first dates, most of them bad. They ranged from a guy who lied about his job (I didn’t care about his job, but I did care that he’d been dishonest), to one who was so nervous he couldn’t speak, and a man who neglected to inform me that I was on a date – I thought I was going to a business meeting. Dating, as far as I was concerned, was torture.

But when I moved to NYC, I learned the art of the successful date. My British friends urged me to online date, my NY friends warned me off, as Manhattan men never call for a second date. Rather than feel depressed, I saw this as an opportunity. After all, I was in NYC temporarily and to get involved in a serious relationship would have been too complicated.

However, I did want to make the most of my time in the city and meet some interesting people. What better way than by dating? Every date a different venue, so I really got to see the city, and every date with a different and interesting guy, whom I would never have otherwise met.

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Safe in the knowledge that the men weren’t going to call me again, we were free from the awkward first date conversations about relationship expectations and I could ask them anything I wanted.

Because I knew they wouldn’t call, I didn’t have to worry about whether they liked me or not; it didn’t matter. It led to some really revealing and fascinating encounters. And guess what? They did call for second date. Why? Because they had fun.

Ambitious NY women who are looking for a husband book their dates like business meetings – often booking one at lunchtime and two in the evening. The men have 20 minutes to prove their worth as prospective husband/father material before the woman ticks them off her list and leaves for her next appointment.

My only agenda was to have an interesting night out, and because of that was relaxed about the outcome. It meant that I didn’t need to stress about getting my hair done, or buying a new outfit for a date. I just combed my hair, brushed my teeth and arrived on time and with a smile.

I went on a lot of dates and met many men (some of whom are now friends) and, after a lot of trial and error worked out how to guarantee a good date:

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Choose your date carefully
Approach women who look and sound interesting, but don’t put pressure on yourself – if she’s not ‘the one’ it doesn’t matter; worst case scenario is you spend a couple of hours having a drink with someone. If you have a bad feeling about someone before you meet, you shouldn’t meet – listen to your gut instinct. Remember, your primary aim is to have a good night out.

Decide on a venue
If you take control and suggest a venue when you ask a woman out, you will immediately impress her. Many men are far too hesitant to suggest somewhere, which leads to frustrating and time wasting back and forth emails as you negotiate where to meet. This is definitely an occasion where it pays to be masterful. Don’t feel you have to try to impress her with an expensive restaurant. A cosy and casual café will do just as well (unless you prefer dating materialistic women). Have a list of places you’d like to go and things you’d like to do, then even if the date doesn’t lead anywhere at least you’ve ticked something off your ‘Things to Do Before I’m…’ list. If a date was being slow to suggest something, I would, which meant I went ice-skating in Central Park, rode the Coney Island roller coaster and went to a movie restaurant that was showing Dirty Dancing on four screens. It was revealing who was willing to roll with it, and who wasn’t. Needless to say, most of the good guys didn’t hesitate to roll (or ride) with me.

Don’t go for dinner
my first NYC date was a disaster. The guy had lied about his age, height, and job (and I’d originally agreed to a date only because I didn’t want to be rude). I knew as soon as I saw him that we had nothing in common, but we had a table booked. And so we had an excruciating dinner, which lasted around three hours as he insisted ordering three courses. Arrange to meet for a drink, and then escalate it to dinner if you are enjoying each other’s company.

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Arrive early and sit somewhere obvious
Aside from the fact that it’s rude to be late, it pays to be early. You can scope out the bar and find a good seat. Arriving with ten minutes to spare means that you can relax and clear your mind of the day’s irritations so you can focus on your date conversation. And it’s always more stressful to be the one who arrives second as you have to scan the room while your eyes adjust to the light, not quite sure whether this person or that is your date (this particularly applies to blind and online dates), and leaves you flustered. Arrive first, keep an eye out for her and greet her with a smile and a wave so she doesn’t feel self-conscious.

Have a conversation starter planned
The start of the conversation is the most awkward. Combat this by launching into the ‘middle’ of a conversation, as you would when meeting a friend. For example, “I was just next door looking at some architecture books – I’m thinking of doing a course/building my own place,” gives her something to respond to that is more stimulating than “Did you find this place all right?” Before you know it you’ll have been chatting for an hour.

Remember that it should be a dialogue not a monologue
Ask her questions and listen to the answers before responding. Try not to express your opinions as fact. If you feel strongly about something, say so, but ask her what she thinks too – you’ll find out much more about your potential compatibility.

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It’s not a confessional
I’ve been on a date with a guy who told me his girlfriend was moving out of his apartment the next morning, one who cut the date short to go and have dinner with his mother and another who told me he had just been diagnosed with cancer. Keep the first date light (this doesn’t give you a license to lie) and fun – save the important stuff for the second date (if there is one). If you don’t have a second date, it doesn’t matter, and you haven’t ruined a good night out.

Notice her body language and react accordingly
If she’s leaning towards you, playing with her hair, smiling, and sitting with her knees pointing in your direction, she’s into you. You can afford to touch her on her arm as you talk or put your arm around her as you leave, but don’t come on too strong. And if she’s leaning back, arms folded, tread with caution – she’s not yet convinced. It’s not necessarily a lost cause, but you have more work to do. Are you dominating the conversation or letting her do all the work? Remember to listen!

Always have a second drink
It’s rude to leave after one – Seriously. If you’re bored, ask better questions, play pool or something (preferably with your date).

If you do not want to see her again
Say it was lovely to meet her, and shake her hand when you part – she’ll get the message. Don’t say you’ll call and then don’t.

If you do want to see her again
Send a thank you email or text the next day and suggest another date. “Would you like to go to see this exhibition/play/movie?” is better than, “we should do it again.” If she doesn’t respond, she’s not feeling it, so don’t chase her. Move on.

Alex: Thanks for the post, Nicola!

If you have gotten this far, please do leave a comment with your thoughts, and don’t forget to subscribe to the RSS feed for free!

Talk to you soon.

Beautiful images by Wollbinho and Bostonbill.

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8 thoughts on “The Art of The Successful First Date – Even If She’s Not ‘The One’

  1. Scott D

    To me this is among the most valuable posts yet… too many of us (especially guys, I think) are so concerned about making ourselves look eligible and worthy, always striving for that second date, that we forget that the here and now is what’s important. It’s also really good to get some inside information from women, so if it’s possible you should try to get more female guest posters or interviewees for their point of view, Alex. And thank you both, Alex and Nicola, for the great article.

  2. Yavor

    When you think about it, these tips are kind of obvious, but not many people do them.

    For example – always choose a venue in advance. As a bonus – choose someplace you are comfortable going.

  3. Ted

    Fantastic article, Nicola. I love the advice from a woman’s perspective.

    A quick heads-up on a typo:

    In the “Notice her body language…” section, fourth sentence:

    “It’s necessarily a lost cause,…” should probably be:
    “It’s not necessarily a lost cause,…”

    At least, I hope it’s a typo. ;)


  4. Marie m

    For a first date – or a second, or third… – it is really important to pick a venue that you’re comfortable with. I also agree that it’s so important to notice body language. I read an article on each of these topics on http://www.findtruelove.com, an online dating site I recently discovered that I really like.