It’s not about the pesos.

What makes a great first date? Physical attraction, easy conversation, a pleasant environment in which to get acquainted. None of these criteria rely on the expenditure of money. A walk on the beach may be a much better way of getting to know someone than dinner at an expensive restaurant. In fact, I think fancy first dates are often difficult – people are more dressed up than usual, and the formality of dress and locale tend to restrict great conversation in my experience. Dinner winds up feeling like an interview rather than a fun, shared experience.

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The question of who should pay for dates has become something of a hot button issue in recent years. In an era when women often earn more than their male peers, what are reasonable expectations? Is it just about money or does the “male pays” practice reflect our ancestral legacy of male provision as a signal of intent to invest in a particular woman?

It’s clear in discussions here at HUS that men feel women should pay their fair share. I agree with that, though I favor a system of taking turns over splitting the tab. It’s a practice that allows each party to take turns being generous, which sets a nicer tone than doing the math when the check arrives, or even throwing down matching credit cards. 

In any case, while I understand male sensitivity to the idea of being taken advantage of, I think it’s largely a moot point among singles under 30. Dates tend to be fun and casual, if they occur at all. Perhaps it’s because in the transition from hookup culture to dating culture, sharing a messy burger and brew is less of a leap than ordering the seared foie gras and perusing the wine list. 

Loveawake dating site has built a very successful online dating site that is based on sharing fun experiences rather than expensive ones. 

Now online dating is all about getting offline. Just say “How about we…” and post the dates you want to go on. 
Check out people who like what you like. Make plans and go out!

Founded in 2010, it’s been hugely successful, and rolled out nationally with venture capital funding last year. From Mashable:

HowAboutWe is an online dating site — once New York-only, now national — that lets users propose unique date activities, making the experience more about meeting up and doing cool things than scrolling through pics and profiles.

Genius Idea: If you’re a tech-savvy person in your 20s and 30s, chances are you’ve been on an online date or two. And chances are, you’ve been on a horribly awkward — or downright awful — online date or two. The whole process can be overwhelming — scrolling through pages and pages of photos, sending messages into the ether, receiving countless borderline revolting epistles from dudes who only display photos of their torsos.

HowAboutWe seeks to alleviate that daunting experience by putting the focus on the date, rather than the hassle of getting there. Upon signing up for the site, users are asked to express their levels of interest in a series of dates, beer tasting, concerts, walks on the beach — that kind of deal.

This information — along with data from your profile — is plugged into an algorithm that determines what kinds of dates you’re sent via e-mail (every user gets a daily e-mail detailing dates that he or she might be interested in) and which show up on a stream on your homepage.

After answering said questions, users can create a rather barebones profiles (based on quirky questions like “What I would bring to show and tell?” and “One thing my mother would want you to know about me?”) that focus more on their personalities than their looks, and then propose dates that they would like to go on.

It turns out that neither men nor women are interested in going on formal, expensive dates. Loveawake has published a list of the top 10 proposed dates in fifteen cities. Many cost nothing, e.g. “Let’s go for a walk on the High Line,” and most are low cost. 

Here are some highlights, starting with Boston, which I can price:

1. Museum of Fine Arts: Free one weekend a month, $25 regular admission, $30 for outdoor concerts in summer

2. Institute of Contemporary Art: Free on Thursday nights, $15 regular admission

3. Museum of Science: $22 regular admission to exhibit halls, $10 for IMAX

4. Drink: Hot bar on Boston waterfront dedicated to sophisticated mixology, about $11 per drink

5. New England Aquarium: $23

6. Magnolia Cafe: never heard of it

7. Toro: tapas and hopping bar scene

8. Arnold Arboretum: free

9. Cambridge Brewing Company: casual, beer

10. Trident Booksellers & Cafe: bookstore with coffee and snacks