I Want to Take a First Date to Lunch During the Work Day. Why Is This a Terrible Idea?


I met a girl online and we are meeting for the first time for lunch this week. We talked on the phone for hours already and she texts me often. We seem to connect very well.

Are there any tips you have for me to make meeting her a bit more special? We are both busy people, so the lunch idea came up, because we both work near one another in town. Since this is the first contact in person I will have with her, I didn’t want to make it too high of pressure or a formal date.


Dear Matt,

My philosophy for first dates was first outlined in “I Can’t Believe I’m Buying This Book – A Commonsense Guide to Successful Internet Dating”. The chapter was called, “How Caffeine Kills Chemistry, and Other Controversial Theories on Dating”, and, in essence, it said this:

If you can’t kiss at Starbucks, what’s the point of going to Starbucks for a first date?

Ready for Lasting Love?
Ready for Lasting Love?

There was more… but that was the gist of it.

While I won’t retract my theory entirely, I do have some modifications I’d like to make.

I am still firm that slowing down is an essential component to making your first dates pop.

The problem with online dating is its illusion of instant gratification. Guy gets rejected by 100 women and becomes convinced that if he only goes FASTER that he’d get a chance at a first date. Woman emails a guy for a month, only to find out he’s 5 years older and 30 lbs heavier than he stated; she becomes convinced that if she only goes FASTER, she wouldn’t have wasted so much time.

If you can’t kiss at Starbucks, what’s the point of going to Starbucks for a first date?

The reaction to our respective failures is to cut to the chase TOO fast. As a result, you email total strangers and say, “You look cute. Let’s meet at Starbucks on Tuesday”. But you’re missing an important part of the dating process – namely, the getting-to-know-you part. By circumventing the normal process of courtship – you’re skipping an integral building block for a first date.

Believe me – I get why you do it. You’ve been burned. You’re busy. You don’t want to waste time. Got it. Then you have no one but yourself to blame when you go on a series of blind dates with unscreened losers. That’s what you get when you meet strangers after only a brief email exchange.

Matt, to his credit, didn’t do this. In fact, he spent hours and hours on the phone, building trust, rapport, and comfort. What does this mean for Matt? It means that if his date’s considering 5 guys from Match.com right now, and 4 of them are emailing her: “You’re hot! Let’s meet up!”, Matt’s going to stand out, just by being a little patient. Restraint is a very powerful tool in a man’s arsenal.

Just by taking a little time to make a woman comfortable – a few emails, a couple phone calls – Matt can earn the right to pick her up at her place for a Saturday night date. The same exact woman who would otherwise insist that a first date meet her at a coffee shop. If you doubt me, I have a few hundred examples suggesting otherwise. Slowing down really does result in better first dates.

But you already know this, Matt. Thus, your real dilemma is in figuring out what a good date looks like for you. And that’s personal. For some people, the ideal date IS coffee/lunch. A quick meeting to determine basic physical chemistry. Well, if that’s the case, then you don’t need my advice. Find a place that’s mutually convenient, well-lit, and inexpensive. Ask questions. Pick up the check. You’re all set.

So what’s wrong with disco bowling and beer on a Friday night? What’s wrong with mini-golf on a Saturday afternoon?

My question to you is this: do you LIKE lunch dates? Low stakes, low price, low romance, “I have to be back in my office in an hour” interview type scenarios? God knows, I always HATED such dates. And if you find them lame and you want your first meeting to have a bit of a spark, you have to work backwards from how you want your date to end. For me, ending on a kiss was important. Thankfully, you’ve already earned enough equity with her to take her on a real date that doesn’t involve a midday break.

So what’s wrong with disco bowling and beer on a Friday night? What’s wrong with mini-golf on a Saturday afternoon? What’s wrong with night-time appletinis at a speakeasy on Saturday night? What’s wrong with taking her hiking (or sledding?) on a Sunday afternoon?


None of this is formal. None of this is high pressure. None of this is terribly expensive. None of this means you’re locked in to six hours together. All this establishes is that you’re a man with a plan. A little creativity and atmosphere goes a long way in setting the TONE of the first date.

And if I have any objection to coffee/lunch, Matt, is that it is the wrong TONE for romance. It’s the wrong tone for laughter. It’s the wrong tone for anything but an interview that assumes failure. You don’t set up a half-hour $3 date if you think it’s going to go swimmingly well.

Take it from a guy who has gone out with hundreds of women:

If you treat her special, she’ll be special.

If you show her a good time, she’ll have a good time.

If you give her a chance to shine, she’ll have a greater opportunity to shine.

And if you want to get a kiss, you’re much more likely to get it at night. I have not once had a great date at the Coffee Bean or Quizno’s or Jamba Juice or the Daily Grill. It could be just coincidence, but the sample size is large enough to conclude that certain settings are more conducive to romance than others.

Be the generous guy who really wants to show her a lot of fun, and I’ll bet you have a lot of fun, too.

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