Hey Romeos,

Valentine’s Day is coming around fast and Dave has some comments about it. Read on:

Dave: One question guys are always asking me is for date ideas – especially a first date (like they really want to impress some woman on the first date).

Part of my advice to them is not to spend a lot of money. It makes them look like a tool, like they’re desperate, and trying to buy some woman’s attention and affection (because they don’t have anything else to offer). Besides, that, it sets the pattern. If go all out on the first date, but not on future dates, suddenly you’re a cheapskate. Another part is to avoid chick flicks.

A few weeks ago, someone asked how much money is “a lot.”

And starting a couple of weeks ago, several people began asking what to do for a first date on Valentine’s Day. Some of them have been plotting for weeks or months to have their first date with someone on V-Day. Why they’d do that is beyond me. It’s one of those damned-if-you-do and damned-if-you don’t situations.

Here are my responses:

It depends on how old you are, what you do for a living, where you live and what you’re going to do on the date. The point is that she shouldn’t think that you might be going all out to impress her with where you go.

If you’re a surgeon, “a lot” is different than if you’re a college student (and the temptation to spend too much might be greater, too). If you’re an MD, you’ll probably spend more than a college student. If you’re in Manhattan (NYC, not Kansas), you’ll probably spend more (maybe on taxis alone) than you’d spend if you were in Norman, OK, where I spent four years in college.

If you’re going to eat, look at the restaurant ratings. If it shows the price as $$$$$, you probably don’t want to take her there on the first date. Maybe not even a $$$$ restaurant. Maybe you know a cool little Lebanese restaurant that has the best calamari in town. (And if wine is involved, go with the house wine or something “inexpensive.” Don’t ask what vintages of Chateau Haut Brion they have in the cellar.)

Btw, some guys like to go to places where they know their way around, they’re known by the employees, know what to recommend from the menu, maybe get a little extra service, etc. I wouldn’t say that’s absolutely necessary, but if you don’t, it wouldn’t be a bad idea for you to scope out the place before asking her, rather than just pick a place off the Internet. That can help to avoid the occasional nasty surprise when something isn’t what you expected it to be.

Personally, I’m more inclined to keep it simple – like burgers (NOT McDonalds or Burger King unless you’re on a really tight budget), ribs (although they can be messy) or pizza, if it’s for dinner. More often than not, pizza is my go-to plan.

And I’d prefer to do something that provides an opportunity to talk and get acquainted, which pretty much eliminates a movie the first time out unless you have dinner first.

If you’re going to have pizza and a couple of beers, $50 or so should be more than adequate just about anywhere. If you’re going out for dinner and drinks (or even just drinks) $50 won’t go very far.

It should be about what you’d spend on a “typical” date – or a typical Friday or Saturday date if it’s on a Friday or Saturday. You don’t want to spend enough that she thinks you’re throwing money at her or trying to impress her. Nor do you want to set the bar so high that you can’t match it with some regularity.

Valentine’s Day isn’t exactly a gift to guys. More than anything it’s another opportunity to screw up.

Although it’s been on the calendar for centuries, it wasn’t until the 1800’s that it became a symbol of romantic love. Before that it was another religious holiday (kinda like All Saints Day) that was celebrated mainly by the Anglican Church in England. (Yeah, I’ve heard the story before, but I checked the net to make sure my facts were straight.)

It was made popular by the greeting card companies, who saw it as a way to create another big holiday (second to Christmas) when they could sell cards. Even 50-60 years ago V-Day was mostly about the cards – and the kids.

Then some company started making those little heart-shaped candies that taste like chalk and have semi-mushy messages printed on them. The chocolate companies also saw it as an opportunity. In 2008 the average V-Day expenditure crossed $100. Now it’s closer to $150.

The two days I’d never ask a woman for a first or second (and maybe not even a third) date on are her birthday and Valentine’s day. I’d spend the evening sitting at home and watching tv first.

Here’s why it’s an opportunity to screw up – especially on a first (or second) date.

First, the message on the cards is either too mushy (more likely) or not mushy enough.

Even if you send cards to half a dozen women, you can only spend the evening with one of them. So what does that say to her? It says that you consider her your best (or only) option – or at least the best one who didn’t already have plans.

You might as well walk up to a woman in a bar and say “I think I wuv you.” (Hell, if you said it with the right silly grin, you’d be better off doing that.)

And you can’t get the amount that you spend right. If you don’t spend a lot, she’ll think, “Okay, I’m your number one, and pizza and beer is the best you can do? Where’s the champagne?” If you take her to dinner in a nice restaurant on the first date, you’re trying to impress her, which makes you look desperate. Lose lose.

You don’t want to spend too much on a first or second date (or make a habit of throwing money at women). It makes you look desperate and makes her wonder what shortcoming you’re trying to compensate for. Plus it causes her to expect you to spend a lot on subsequent dates. But it’s Valentine’s Day, and women expect something special.

That in itself is a no-win situation.

Even if you’ve been in an exclusive relationship for a while, you either spent too little or too much. After all, this is the big lovers’ holiday…

Generally I avoid chick flicks. The main exceptions are birthdays and Valentine’s. But since 50 Shades of Grey (the movie) opens on V-Day this year, that might be a good idea. It could be a killer mood setter. Just include a little time for conversation and getting acquainted.

Clifford: Dave brings up a number of points that most of us guys have had to consider at one time or another in our lives.

There are probably endless comments that can be made about first dates, so I will restrict myself to a few relating to Dave’s comments. Firstly, and here’s something controversial about first dates that you may not read elsewhere, in terms of how much you should spend on a first date. I personally don’t do this anymore but I know that there are a lot of guys (and that used to include myself) who will spend a lot on a first date for one good reason – it worked most of the time. It didn’t work all the time, but when I used to do this my dating skills weren’t that good and taking the girl out for an expensive dinner in a nice romantic restaurant led to success (usually at least a make out). Clearly this, as Dave says, may be sending the wrong message to the girl including building her expectations that you will be taking her to expensive places all the time. Personally, that really wasn’t how it played out for me – subsequent dates were usually at more reasonable locations but I wasn’t against the idea of going to a nice place once in awhile. I used to know someone who would take a woman out on a first date to a coffee shop / restaurant in a lower class part of the city (not a dive but a very inexpensive spot where you would have a selection for $5-6 of dinner meals). He wanted her to get the message that she wasn’t going to be dining at the Ritz when she went out with him so she better be there because she liked him and not for what he was going to buy for her.

Today I will take a woman out for coffee or drinks – dinner is a bit much for a first date. Alternatively, I may invite her over to my place depending on how the interactions have gone. There are a number of dating coaches who will teach that you should just have her come to your place for the first date, but it’s been my experience that that can be too pushy for some women and given the choice between insisting on her coming over (which in my case has sometimes led to her not wanting to see me period) and being flexible enough to go for coffee or a drink, flexibility has been a better strategy.

In terms of Valentine’s Day, inviting a girl out for a first date on V-Day immediately lets her know that there is no one else in your life. There’s clearly no other woman you are going out with on V-Day and that’s why you could see her, isn’t that right? A first date on V-Day is like a first date on a Saturday night – it sends the message that you don’t have another date that night. An important rule is “always let them see you living large.” In other words, even if nothing else is going on in your life, no one has to know that. You don’t have to lie, but you don’t have to say much either. Keeping some mystery about yourself is an art – you need to find the balance between not saying too much and being secretive in a suspicious way.

As for movies on a first date, conventional community advice is that this is a really bad idea as you can’t really talk and get to know her while at the movies. However, an alternative view of this comes to my mind of a guy I used to know who just had a playful way about him and taking a girl to the movies was an opportunity for him to do a lot of non-verbal physical things which created fun and intimacy without a lot of talking.

There is, of course, also Johnny Soporno’s way of handling first dates. He will tell a woman that he keeps first dates to 30 minutes. If the first date goes well, then they can immediately go on a second date. (This is a creative way of dealing with women who won’t sleep with you on the first date.)

It may be short notice, but I would like to get some ideas from you about what you do that might be different for Valentine’s Day.




I have been fortunate enough to have been able to present a lot of great material in the cliff’s list newsletters and now on the website that have made a significant difference in many guy’s lives.

Leave a Reply