How to Get the Most of Your Coffee Dates & Start Establishing Real Connections

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How to Get the Most of Your Coffee Dates & Start Establishing Real Connections


How to Get the Most of Your Coffee Dates & Start Establishing Real Connections

Creative Pursuits


This is part 3 of my business bff series. If you’re interested in this topic feel free to check out part 1, Finding Your Pack and part 2, How I Found my Business BFF & Created My Own Mastermind Group.

Raise your hand if you’ve been eyeing a fellow creative entrepreneur on social media or have seen someone at repeated networking events and you’re ready to take it to the next level. As someone who has gone on several coffee dates, it took me about a year or two to finally get to a point where I have a network I can rely on and real business friends.

Before the Coffee Date

I used to have coffee with anyone and everyone who would ask. But after seeing that not all these coffee dates lead to real connections I started getting a little bit more picky. I’m still down to have coffee with people but my prerequisite is that we have to had met at an event at least once or have had some type of connection or conversation on social media. If we’ve exchanged a few words on social media then I’m totally down to meet you in person. But if someone reaches out to me out of no where then I’m more hesitant. Social media for me is a way to test the waters to see if we even have anything to discuss. Creating a network is like dating. So before you go out and start scheduling coffee dates all over town, first follow people on social media and start connecting with them there. That’s my own personal suggestion but if you have a contrary opinion by all means do share!

Coffee with a fellow girl boss

Since working from home it has become really important for me to cultivate a network with other creative entrepreneurs. Being a solopreneur can get lonely at times so I’ve made it a priority to make connections with other solopreneurs with whom I can foster a community.

Is there someone that you’ve been following online for a while or have seen at networking events? Reach out to her and plan a coffee date. Keep it casual but take this opportunity to get to know the other person in a way that you can’t get to know them in 140 characters or at networking events. I’m pretty much an open book so I don’t mind spilling the deets of my biz. You might not be the same way but I still encourage you to open up and allow yourself to get a little vulnerable with the other person. Opening up and vulnerability are what create connections with others. You probably already know how/when the other person started their business or creative project but you probably don’t know what feelings arose when they were doing that or if they had any resignations before starting.

Stay Connected

If you are serious about connecting with people and bringing your networking skills to the next level then it’s important to follow up. Did you have a great conversation and good time with this girl boss? Then follow up via email. A second coffee date or meeting might not happen for a few weeks but that does not mean you can’t stay connected. Be active with them on social media, comment on their posts, email them articles you think they’ll find useful and maybe even incorporate texting. This is how connections and friendships are created. So get out of your shell and you won’t regret it! But always be mindful that relationships take time to cultivate.

Skip the Coffee Date

Okay so I know this post is how to have better coffee dates so this may sound contradictory but bare with me here. Coffee for a first date is a great place to start but imagine if you only went on coffee dates with your boyfriend/girlfriend or friends. Wouldn’t you be like “um can we like go to the beach or do something else for a change?” There’s something about coffee dates that feels too much like a date and too much like an interview. The first time I had coffee with my fellow girlboss, Amy, we were so into our conversation that she invited me to a bonfire later that day. The introverted me was hesitant to say no thinking that maybe I’ve already had enough social interaction for the day but by going out of my comfort zone and hanging out in a non coffee shop setting allowed us to talk about things besides work. It’s casual settings like the beach or a hike (which Amy and I have done both) that allow you to let your guard down. It’s important to have friends that you can talk to about your work life but what’s helped me really establish relationships is being able to talk about personal things as well. Amy and I always dish out about our boyfriends, how we partied all night last weekend, Amy’s recent engagement, and much more. By infusing those personal elements we’ve been able to cultivate a friendship and not just an acquaintanceship.

Coffee with Someone You Admire or a Potential Mentor

I remember one of the first times I was asked out to coffee from a USC design student. I was so flattered because it wasn’t that long ago that I was the hungry student eager to learn everything from everyone. What I liked about this student is that she took the time get to know as much as she could about my business. I wouldn’t be surprised if she also took the time to read a few of my blog posts as well. If you are having coffee with someone who you would like to learn from or have them be a mentor, be prepared with questions or topics you’d like to discuss. Do your research ahead of time so that you can go deeper with stuff you could have found out online. When you reach out to that person let them know what your intention for your coffee date is but keep it casual. “Hey Diane, it’s been great seeing you at Worthy Women events lately and I love where you’ve taken your biz, Soiree du Jour. I’m thinking of taking my side hustle to full time hustle and I’d love to have a chat with you about it, drinks on me!” As someone who has been on both sides of the conversations, I think it’s important to note that this person that you admire does not have all the answers. Have you ever met a celebrity in person and thought to yourself that you imagined them to be taller (the first few times I saw Heather Graham in my yoga class I didn’t even recognize her because she looked like a regular person, gorgeous of course but everyone in my yoga class is gorgeous)? The same can hold true for meeting someone you admire.

These are a few tips and tricks I’ve picked up along the way. I’m always looking for new coffee shops and places. Do you have any cool coffee shops you’d recommend or non-coffee dates you’d recommend? What’s your coffee drink of choice?

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  • Great post! These tips are very helpful especially because dates can get very awkward when you do not know what to do. Keep up the good work and I wish you all the best.-Chris Thompson

    • Hi Chris! I totally know what you mean by those awkward moments. I think putting yourself out there to people you admire can be a little awkward and nerve-wrecking. It’s no different than dating! Thanks for your kind compliments and I’m glad you’re finding my tips useful!