Name: Brian Phillips
Age: 35
Location: San Francisco, CA
Why we care: After a career at PayPal, Brian Phillips founded Thread.com, a dating site that allows users to connect with friends of friends using Facebook. He's still single, but at least he's not afraid to throw money at the problem.

Tell me about your first date.
I was 15. I took her to this very cheesy restaurant in Ohio that had steaks. It was really over the top — the type of restaurant elderly couples would go to for their 50th wedding anniversary.

What did you spend?
About $60, which is a lot for a kid in high school. I used money I saved from a delivery business I started. There was this deli that would have this huge line on Sunday mornings, and I struck up this deal with the owner and the people who went there to deliver their breakfast and New York Times to people at their homes. They'd tip about $5.

When dating became a regular thing, what types of things did you like to do and how did you budget for your dates?
In college, I didn't have to spend a lot of money because we'd have study dates at the library, or go biking. Sometimes, I'd take a girl to the student union where there was bowling, and I knew that if a girl had fun, that meant that she wasn't very high-maintenance. I'd buy a $5 pitcher of beer and we'd have that for the night.

Are you a flowers-and-candy type of guy?
Flowers are a terrible idea. It shows you're way too interested. Plus, flowers can be really expensive. A dozen roses is like $65.

When you got more successful, did you spend more on dates?
A little bit. I definitely stopped thinking about how much a date would cost. One of my favorite things to do after I've been dating someone for a while is to go on what I call a "date-cation" — a weekend away somewhere. One weekend, I took a girl to Las Vegas and we went to see Cirque du Soleil and to a really nice steakhouse for dinner. When I'm in Vegas, I like to take the same amount of money I spent on dinner and gamble it, because if you win, hey, free dinner. The steakhouse dinner was about $500, so I put $500 down at a blackjack table. I got blackjack, so not only was dinner free, but I made $250.

Do you think you should always pay for a date?
Yes. Women are the prize and they're the one usually being chased. More importantly, I think it's good to be chivalrous.

What's the biggest mistake people make when it comes to money and dating?
The number one mistake is to create awkwardness by fighting over the bill. If one person really wants to pay, and they asked you out, let them pay. But make sure you thank them, and if you're having a good time with them, tell them you'll get it the next time. Also, I have a lot of girlfriends who feel bad when they go out with a guy who pays for a date even if she didn't hit it off with him. Don't feel bad. Your time is valuable, and they'll understand.

What's the biggest mistake you've made when it comes to money and dating?
One mistake I've made is doing things like going on a ski weekend too early on. You can have just a good of a time going hiking, or making dinner.

What was it that got you interested in starting a Web site based on dating your friend's friends?
Many friends of mine were single, and I kept thinking, "that's impossible, you're great!" A good amount of all marriages have come from friend introductions. I've told my friends if they introduce me to my future wife, the reward is a first-class, five-star trip for two for anywhere in the world.

How much are you willing to spend to find love?
Money is no object. How do you put a price on love?

Earlier this week in Other People's Money: 23-year-old mayor Justin Nickels answered invasive questions about his personal finances.


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