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How to Meet Men & Date Like a #LADYBOSS


Alessandra Conti

FRIENDS HAPPY 2019. I can hardly believe it is finally here! WOWOWOW. As we look back on 2018 we are in AWE of so many things.

Here is a message from Kait, our host:

One year ago I shifted the course of my vision. I stepped into murky water with NO where to see where I’d end up. I felt prompted to start a podcast on DATING… you know… just one of the most complex, unknown, opinionated topics out there.

I DID NOT feel very qualified.

I HAD no idea where to begin.

I found myself thinking “who would listen to a podcast on Christian dating? Won’t I run out of topics? How would I ever get guests on? I’m not credible to even do this!

But friends… when you step into the unknown with FAITH, God can do amazing things. He asks us to take his hand and trust, We might only be able to see the next step ahead, but that’s all we need to see. Faith doesn’t make things easy, it makes them possible!

Now in one year… BECAUSE OF YALL! we have had over 150K downloads, launched 37 episodes, have landed in the top 50 christian podcasts and interviewed some of the MOST amazing people.

What I have to say is this has been the most rewarding, exciting, and growing journey… and I am SO THANKFUL FOR ALL OF YOU GUYS for sharing the podcast, listening each week, writing reviews, telling your friends. You all mean the world and I can’t wait for what is in store for 2019.

Now today, we are so excited. We have had SO many ladies writing in asking questions about knowing where to meet guys, how or if they can initiate, ALL of it. So today we brought the amazing Alessandra Conti on to talk about it ALL.

Alessandra is a Celebrity Matchmaker and Co-Founder of Matchmakers In The City. You may remember her sister Cristina just a few months ago! They are two girl bosses who co founded this incredible matchmaking company. Matchmakers In The City was praised by Patti Stanger, Millionaire Matchmaker, as “the new generation of Matchmakers.”  Aly is also a Matchmaker behind MTV's Are You The One, and is a frequent media guest. She’s also the go-to Celebrity Matchmaker for Vivica A and has been on  CBS's, Face The Truth, and has been featured on Celebuzz, The CW, and Fox News among others. She has 7 years experience in this friends and  has worked with thousands of single men and women.

Yall are going to get a TON out of this episode…Also we have a special discount code for you if you’r interested in matchmaking. Use HEART to get a discount on your membership at, and find out more at 33:00 in this episode!

Where in the world do we meet a quality MAN?

  • The first step is to BE AWARE everywhere that you are.
  • Be present. Put your phone away and look around you.
  • Also, CHANGE THINGS UP. Instead of going to your typical coffee shop, go to a NEW coffee shop.
  • Anywhere there are LINES. Aly says, “Lines are a single woman’s best friend.
  • DOG PARKS- such a great place to meet people (plus play with cute dogs, #areweright!?)
  • CHURCH- Volunteer places (hello serving!), young adults group, community group
  • If you say “there are no good men at my church”, you could be stuck within just your friend group, find other friends! Even go to OTHER church’s events.
  • EVENTS. EVENTS. EVENTS. Go to EVENTS! Aly sends her team to events and calls them “recruitment events”.
  • Also… birthday parties! Great place to meet new people.

Is it too forward for a woman to make a move?

  • No it is NOT!
  • Many women feel powerless because no one is approaching them… BUT there is a solution!
  • Men are not mindreaders, we need to do something called DROP THE HANKY!!!
  • Drop the Hanky is a term from the Victorian Era, when women used this to meet eligible men… and it worked swimmingly well!
  • How can we do this in MODERN day? We need to BREAK the ice. It is not about playing games or doing an entire SONG & Dance.
  • Aly recommends breaking the ice in an indirect way… make a connection point. Here are the steps:
  • Get in Proximity
  • Ask and indirect question like “What’s your favorite coffee here?” Simple, easy, approachable.
  • Follow Up Question such as “Are you from around here?” to CONTINUE the conversation in the interaction.

What about MEN at CHURCH? You do something VERY similar.. find a connection point, that can be indirect. BREAK the ICE!

  • Both Kait and Aly agree it is NOT too forward. It can be as simple as “Didn’t you love that sermon?"
  • Also pay attention to other body language indicators like body language and eye contact.
  • What do we do if we clam up and get super nervous?
  • First of all, embrace you’re awkward! Awkward can be endearing and CUTE, so it’s okay.
  • We tend to put up armor and try to be something we are not. But we have to open up that armor and be the “kookie”  person that we are inside.
  • BE UNASHAMEDLY YOU.” Be willing to be vulnerable and be allow yourself to be seen.
  • Aly also says " Instead of waiting for the moment with the perfect Ken Doll and dropping your hanky then, do it consistently with other people. Practice makes perfect.” This doesn’t mean you have to seriously date those people, you just have to exercise being comfortable with dropping the hanky more regularly!
  • We have to work to “de-mystify” the idea of approaching a man. Repeat to yourself “THEY ARE JUST A PERSON.”…we spend too much time building someone up in our minds.
  • Kait also says, “It doesn’t mean it’s YOUR person, just because you have a crush."

What about when women are TOO INDEPENDENT and possibly too into our careers?

  • Often times we give off a vibe that “we don’t need men at all”.
  • Over 90% of individuals CRAVE and desire being in a relationship.
  • One of our first steps to conquering this is admitting it’s okay to WANT to be in a relationship. That does not make you desperate.
  • It is all about BALANCE!
  • Some ways to express interest without feeling desperate
  • If you are a ladyboss-LET HIM LEAD! Tune the work switch off, put vacation mode ON. Allow space and give him the opportunity to treat you well.
  • FLIRT- it is OKAY to flirt. We are in an epidemic of NO flirting.
  • Enjoy the MALE presence ladies.
  • Not every person you go out with has to be someone you end up with.
  • Another note to self: Pay it forward with your recommendations friends!

What is your FINALY nugget of dating advice?

FLIRT. first flirt flirt. Drop the hankies. Show interest. You can do this!

Other Resources:

Get a DISCOUNT on your Matchmaker package by visiting and using code HEART !!!

Find Aly on Instagram HERE

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