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How to Get a Second Date (If You’re Poor)


Do YOU know how to get a second date if you’re poor?

A lot of men have asked me how to get a second date when they’re poor or short or [insert other insecurity here].

Ok, I won’t fib to you, these things do matter to some women, maybe even most women, but you can only do what you can do.

In other words, you can change certain things and other things you can’t.

The things you can change you should IF it’ll make your life better FOR YOU.

The things you can’t change, you’ve got to work on accepting because what’s more of a turnoff than any of these perceived flaws is a bad attitude about it.

In the meantime, here’s Wingmam’s advice on how to get a second date if you’re not making bank.

5 Tips for How to Get a Second Date

1. Even if she asks you out, you pay the first go.

Whether it’s a coffee date or a 5-star restaurant.

Hint: Even if you’re not sure it actually is a date, in my book—the man pays. (Smart choice: don’t choose a 5-star venue.)

If you want feminist advice, you’re on the wrong page.

If you don’t pay, she’ll use your poorness against you. Sorry, that’s just the way it is unless she’s under 25 and/or a feminist. You want that?

If you do, then you may be a feminist and are on the wrong site.

Because what if she has a single friend who you might totally dig? You’ll forever be known as the cheapskate.

Antiquated, anti-feministic, even unfair. All true. But, hey, you have a penis. High five!

2. Be sure you want to spend $5+ on a fancy coffee for this gal!

If you think it’s a waste of your hard-earned dollars, then skip it (and her) and keep on keeping on—and move on.

If you think she might be cool, even if not your forever lover, make the investment.

You might learn something new about women. Or yourself. Be curious.

3. Drop the skepticism.

Yes, all of us who’ve suffered through a bad date (or several) feel jaded to some degree.

Unfortunately, jaded isn’t sexy.

Try open-mindedness and don’t talk with venom about all the bad experiences you’ve had.

If you must get your point across, be playful and fun.

Instead of “all the girls I’ve met don’t look anything like the photos they post,” say, “I’m so glad you look as great as your photos!” (Grin/chuckle/wink)

Or instead of “all the women I’ve dated are just into money,” say, “You seem like a woman who appreciates more than just the finer things in life …”

4. Sit “Conversationally.”

When on a (first) date in a café/restaurant, sit facing the crowd not each other.

Or on a park or city bench where you can people watch.

Or at a bar try to sit beside each other at the corner where you can both watch the behind-the-sushi-bar action.

The looking-out-on-the-world-together position avoids awkward silences with a what’s-happening-around-us distraction.

5. Don’t talk endlessly!

Prattling on without giving your date a chance to participate makes you appear self-centred or socially awkward.

Take a deep breath then … tuck (your tongue in), drop (the chatter), and roll (the convo back to her).

Everyone’s favourite topic is generally themselves!

Find out what her passions are not only gives you valuable intel but the positive feelings she has while talking about her passion will be associated with you!

The most important thing about how to get a second date is feeling at ease with yourself.

When you’re comfortable, she automatically picks up on that energy and mirrors it.

And that’s why attitude is more important than money, looks, fame etc. for the right gal.

Many of these how to get a second date tips are from my own past dating experiences and feedback from women.

If you have a dating or relationship question, please visit my coaching page.

xo AJ

p.s. I could really use your help with something…spreading the word, namely my words!

Anna Jorgensen

About the author

Vancouver dating coach for men who love women! ❤️
(Not PC and not a feminist.)

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  1. Hi Anna um well let’s see here goes I finally made it back out into the dating world but has been a rough couple of first dates I crashed and burned on the first terribly by going way too fast the second was beautiful but it was her bday and new to dating after a long span but once again I went to fast for her and she now to has backed off I love to dote over my women but am just not sure what slow means

    1. Always remember this: If you chase, they run. Be interested and interesting not desperate. Because you tend toward being too keen, you should go into the date with the intent to find things you don’t like about the women just to balance yourself out.
      Anyone else reading this should only take this advice if you’re too keen. If you have the opposite problem (no one is good enough) then you should challenge yourself to find things you do like about her.
      🙂 AJ

  2. Dare I say, if you can’t afford $5 for a Starbucks coffee, you need to skip dating and work on making a living.
    On the sitting side by side thing, I think it all depends, keep in mind you can change your position during the date if the vibe says it might worked out better. 1st date I always like to sit facing her to make eye contact. It help me to evaluate how it’s going. The eyes tell a lot. If there’s a quiet moment it can get awkward. Usually it’s something that happened or was said that made the awkward moment happen though. Dating is not a risk free endeavor.
    Later dates I often choose a booth and sit next to her to get some contact going. Starts with a slight brush, then a finger tap on her hand, maybe brush her arm. Depending on how she reacts, it can get cozy. Cozy is kinda the whole point of dating.

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