Who doesn’t have a dating horror story?
Okay, fine… maybe a few of you don’t. If that’s you, congratulations. Truly. The rest of us have endured more awkward dinners, confusing mixed signals, and questionable life choices than any human should reasonably have to in the pursuit of love.
The funny thing is, I’m actually very good at professional networking. People remember me. They refer business to me. They pick up when I call.
Which got me thinking about how the rules for building strong relationships are the same, whether it’s dating, friendships, or professional networks.
The behaviors that make someone want to go on a first date (and then a second… and a third) are the same behaviors that make someone want to take your call, reply to your email, and send you referrals.
Everyone wants to be around people they like. People who make them feel good. And it’s not complicated to be that person. It just takes a little effort and thoughtfulness.
Here are a few lessons I’ve learned from dating that surprisingly translate directly into business prospecting, networking, and building real relationships with potential clients.
Lesson #1: "Hey" Is Not a Conversation Starter
Here are a couple of examples of messages I’ve received in the dating world:
Person 1: “Hey, how’s it going?”
Person 2: "Hey, I saw you’re a Bruins fan! Did you see that insane overtime goal last night??"
You can probably guess which one is more likely to get a response right? That’s because the “hey” puts the burden of being interesting on the other person. There’s nothing to engage with.
It’s the same in networking!
"Just checking in!" or “Hope you’re well” are the professional equivalent of “How’s it going”. And I’ve seen those openers a lot in both the dating and professional world.
What actually works: Being personal, specific and using what you know about them.
Here are a few more examples of better conversation starters than a simple “hey”:
"I see you’ve worked in Europe. What was your favourite part of living abroad?”
"Saw you've joined a new company—how's that going so far?"
Or to a tech enthusiast you could ask “What are your thoughts on the Claude vs ChatGPT face-off?"
You want to open the door to engagement with something specific…about them. Make them feel interesting and feel that you are curious about them, and give them something they can actually respond to.
Lesson #2: It Takes Two To Disappear
You meet someone, maybe at the local coffee shop, get chatting and feel a spark. They say "we should hang out!"
And then you never hear from them. You start to think they've clearly died or joined a monastery!
Or maybe they waited because someone told them to follow the 3-day rule and then life got in the way.
Networking has the exact same problem.
You meet someone at a conference and hit it off. You’re excited to meet a cool person doing interesting things. You exchange cards and say "let's grab coffee!". And then, nothing.
Try this instead: Ditch the three-day rule. Text a quick follow up to build a connection!
Be the person to take the lead! If you’re in the dating world, text the next day. Say you had a good time. Suggest something specific.
In networking, same thing. Email them the next day. Reference something specific from your conversation. Make a concrete next step.
Lesson #3: You Can't Fake Genuine Interest
It’s obvious, in dating and in business, when people are transactional. They ask you a question and their eyes are darting around the room or towards their phone before you can respond.
If you only call past clients when you need referrals, they know.
If you only like their Instagram posts right before you slide into their DMs asking for business, they know.
If you ask "how's the family?" but zone out while waiting to pivot to the topic of real estate, THEY KNOW.
What works in dating AND networking: Genuine engagement! Being curious about people as humans, not prospects. Leaning into that feeling of warmth for the person.
Lesson #4: Frequency + Consistency > Grand Gestures
Imagine if someone you haven’t heard from in a year shows up with 2 dozen roses, just in time for Valentine’s day. It would be very strange.
The business version of this is ignoring your entire client database all year, then sending a holiday gift basket in December. It isn’t going to make them feel special the way you’re hoping.
Grand gestures only work if you have nurtured an ongoing relationship. Then it’s thoughtful and sweet.
What works: Showing up consistently and paying attention. Regular texts (at least once a month), being responsive when they message you, remembering the little details about them.
Lesson #5: Desperation Is Visible from Space
There's a specific energy that happens when you're dating from a place of desperation that repels everyone in your radius.
That same energy exists in networking when you're thinking "I NEED a lead this week." People can smell it. And they want to get away from it.
The fix: Focus on building the relationship. It might take time and multiple touchpoints, but it WILL eventually make it easier to ask for a lead. When you do, you’ll be asking for help from a friend, not someone you don’t know at all.
In the meantime, be confident in the value you have to offer. Confidence attracts people. Leads will come because you’re good at what you do and because people like you.
The bottom line
Most people network poorly because they're focused on today's sale, not on investing in tomorrow's relationship.
Ironically, that “long term” relationship could end up paying off much sooner than you think, because everyone wants to help the people they like.
Making a friend is the most human thing you can do and it just takes a little bit of effort. Being consistent, thoughtful and curious about the other person.
And once they’ve been on the receiving side of generic and boring reach-outs (or silence), they’ll really appreciate you making the effort.
Let Regards be your (work) Wingman!If you’d like to make follow ups easier (in business, not dating), try Regards. It reminds you who to reach out to, suggests what to say based on what's happening in their life, and keeps you from ghosting your professional network. Try it for free (no card required) now. |
PS: BONUS FREE resource launching soon: The Realtor's Network Multiplier - A strategic guide to referrals, relationships, and revenue.
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Why we built Regards
I’m bad at staying in touch. Not because I don’t value people. Its a lot of work, and I didn’t have a system. This started as my fix. A quiet assistant that helped me nurture relationships thoughtfully. When people noticed the difference and asked what I was doing, it slowly evolved into a product. And the love has been incredible. Regards, Khuze
