7 Expert Dating Tips from Silicon Valley’s Top Millionaire Matchmaker

Including the ultimate first-date power play.

7 Expert Dating Tips from Silicon Valley’s Top Millionaire Matchmaker

Including the ultimate first-date power play.

It seems like a curiously analog idea in a world rife with dating apps: hiring an old-fashioned, flesh-and-blood matchmaker. But when you’re a single tech-world millionaire, chances are you need a dating strategy slightly more refined than simply downloading Bumble. And that’s where Amy Andersen, founder and CEO of Linx Dating, comes into play.

She’s worked with many of the biggest names in Silicon Valley to help make their personal lives as successful as their professional ones. And, for what it’s worth, she’s really, really good at it. She’s singlehandedly responsible for more than 100 thriving relationships and marriages, and her clients can pay upwards of $500,000 for her expert instruction.

Over the years, she’s compiled a big list of go-to dating advice that anyone can apply to their lives—no matter the size of his or her banking account—and, with her help, we’ve compiled them all right here. But if you’re going the dating-app route, don’t miss our definitive collection of the best ones should be using.

Dating, matchmaker

1
Don’t Ask Questions You Don’t Want to Answer

On the first few dates with someone, it’s natural to ask a lot of questions. One thing Andersen really wants you to avoid, though, is asking ones that you don’t really want turned back on you. “First and foremost, it feels like you are hiding something,” she explains. “It also feels very off-putting if you ask someone a question, they punt back and ask you the same one, and you refuse to answer it. It’s comes off as very one-sided and unfair.”

So if you don’t want to talk about your childhood, job history, religion, or political views, simply don’t ask your date about these topics—although Andersen is quick to point out that talking about these things early on is often to your benefit. Better to know than not know, right? Speaking of not saying things, here are some secrets it’s alright to keep from your partner.

Dating, matchmaker

2
Make a Power Play

“A ‘power play’ move would be to open up about yourself first and then volley back, asking your date the same question that you just revealed about yourself,” she says.

For example, if you’re divorced, it’s pretty much inevitable that you’ll end up talking about it on the first few dates. Instead of waiting for them to ask you about your relationship history, Andersen says you can actually flip the whole situation on its head and broach the subject before they ask.

Here’s how: “Be the first to bring it up with something like: ‘So a little about me. I was married for 10 years. We got married rather young and in retrospect, I should have waited until I learned more about myself. We had really good times, a beautiful child together, and while I am not perfect at all, I will walk into my next relationship with tremendous insights and wisdom about what makes a relationship a great one. For that, I am so thankful. What about you? Do you consider yourself to be in a good place now?’”

See? Easy. Apply this technique to any big reveal you want to get out in the open, and you’ll end up looking both confident and honest. Now, here are more things you should definitely say on the first date.

Dating, matchmaker

3
Skip Questions About The Past

There’s plenty of time to learn about a potential mate’s past if you keep seeing each other, but what you care about early on should be their present and future, Andersen says. Keep questions and conversation to present and future tense as much as possible, she recommends.

“You never want to dilly-dally in the past. Facing forward invites your date to project and talk about what you want to do together in the future as opposed to focusing on the past—which was clearly not together.” And for more great dating advice, here are 30 things women always love to hear.

Dating, matchmaker

4
Be Yourself… But Really

The number one mistake you can make on a date? Misrepresenting yourself, according to Andersen.

That’s because it can come back to bite you down the line. “In order to find a relationship, you need to be honest about yourself. Visualize an onion. On the first date, the goal is to peel back a layer or two—maximum—about yourself. Share your values, your background that shaped those values, and some of your interests. Invite your date to share their values and passions in life,” she suggests.

With each successive date, you peel back another couple layers. It’s not that you need to tell potential mates everything about yourself right away, but more that being authentic is more likely to lead to a happy, lasting partnership than pretending you have interests or preferences you don’t really have just to keep a new relationship going. That said, here is some more princely dating wisdom for you.

Dating, matchmaker

5
Don’t Fall Into The “Ex” Trap

“You never want to enter quicksand territory by talking about previous relationships beyond a short 45-second sound byte,” she says. “If you find yourself entering this slippery slope, kick yourself under the table, bite your tongue, and immediately project forward.”

If you accidentally veer into this topic, here’s how to turn it around: “…and she was smart and kind-hearted, and I can tell you are very smart and extremely warm-hearted. For that, I am thankful to be getting to know you tonight.”

Bring it from the past to the present, and then move on to the next subject, ASAP. And for even more great dating advice, here’s how to impress any woman.

Dating, matchmaker

6
Pay More Attention to Feelings Than Facts

Sure, you might have a specific idea of what you’re looking for, but instead of just considering your date’s job, where they grew up, and who their favorite author is, give more weight to how you actually feel when talking to them. “Focusing on facts can feel like an interrogation or an interview,” Andersen explains.

The key here is to learn to balance your IQ with your EQ. “Use colorful stories to open up about yourself. Invite your date to open up about themselves through your thoughtful and poignant conversation. Express some vulnerability and you will be well on your way to finding a meaningful relationship,” she adds.

Dating, matchmaker

7
Don’t Get Caught Up in Ticking Off Boxes

Sometimes smart people get caught up in every little detail of dating, which can make it quite difficult to find a suitable partner. “My clients tend to approach dating with the very traits that made them extremely successful in school and in their high-pressure analytical tech jobs,” she says. “And they get way in their heads and this can implode their love lives.”

In other words, they try to think their way through dating instead of letting emotions guide the way. Sound familiar?

“Whether it is long lists of must-have descriptors of an ideal match or a lack of willingness to look past even small things that might not pass muster in a potential match, many of my clients require coaching to learn to tap into their hearts,” she explains. So instead of evaluating potential dates based on whether they fulfill every single one of your “wants” in a mate, Andersen suggests you give them a chance, go on the date, and pay attention to how you feel about them—not just what you think.

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