Dating: Exhausting, Expensive, and Worth it


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My friend nods to me and motions to the bar, “Those girls over there are pretty cute.” We are at a steakhouse in Boston finishing up dinner with some friends. My response: “Alright, let’s go over there.”

Fueled by a combination of determination, a bit of pride, and perhaps a hint of alcohol, I suddenly find myself in a conversation with their group. We talk, get along well, connect on many issues, but inevitably – not one of them is available.

Boyfriend, boyfriend, husband, boyfriend…


We often hear about how difficult women have it when it comes to dating, and that’s true. I understand that there seems to be a severe lack of decent, genuine men walking the earth these days – though I do believe they are still out there. But what we don’t often talk about is how difficult dating is for men, as well.


The onus has always been on men to make the first advance(s) in the dating world. Whether it’s a simple “hello” at a coffee shop or fully immersing himself in a conversation at a restaurant, it is difficult to express the pressure one feels before approaching a woman, or a group of women.

We need to be sharp, funny, attentive, and above all – not creepy in any sense of the word. This takes effort and risk. We don’t know how we will be received when we approach someone, and after some time, we may still find out that she is not available. This goes for online, in person, or however you meet people these days. Hence: Exhausting.

We are getting lunch in the city. A nicer-than-usual place for a casual lunch meeting, but I’m certainly not going to take her to get a burrito, and I enjoy a nice dining experience just as much as the next person, so I figure it’s a win/win.

We have a great conversation. Our values match up. We have similar interests. Everything is moving in the right direction.

How about we go on a date? Like, not a lunch date, but a real date? I ask. “Yes, definitely!” And with those two words, my day is made.

I don’t even look at the bill when it comes, because as far as I’m concerned, dating is not about the money. It’s a shared experience designed to bring two people closer together, and be an investment in your [potential] relationship.


Whatever happened to the “Yes, definitely!” girl, you wonder? She hasn’t agreed to plans since then.

Expensive. And exhausting.

It’s expensive both financially and emotionally because you don’t know who is going to follow through and who isn’t. A first date certainly doesn’t have to be extravagant and I’m not suggesting you take every single woman you meet to a high-end restaurant, but my belief is that the amount of effort you put into a date directly reflects your level of interest in her.

This means that if you only go on “real” dates with women you are genuinely interested in, by default that day/night is going to be a bit pricier than just a casual outing for a couple of drinks. And if you subscribe to the idea of monogamy, that means that only one woman you meet is the one you’re going to end up with. That means you’ll be going on a lot of first dates that don’t evolve into anything, before you find the one that does.


I have witnessed my parents and grandparents, for my entire life, be loving and caring towards each other. My parents are still lovey-dovey and romantic after being together over 35 years. My grandfather still butters my grandmother’s bread after 65 years.

These relationships did not simply fall together effortlessly. My parents or grandparents were not assigned to each other on their day of birth. They all went through failed relationships. They all faced heartache. They all thought life was going to go a certain way – but it didn’t.


They all had to work and put in effort to improve themselves and become attractive to the type of person they would want to be with – as we all do. It was exhausting for them. It was expensive for them. But – it was worth it for them.

It was worth it because as the saying goes, you’ve got to open a lot of oysters before you find a pearl. What is the alternative? To give up dating or swear off love because it’s just too much work? No – you get up, you dust yourself off, and you keep your eyes open for the next person who catches your attention.

It is easy – very easy – particularly in today’s society, to become discouraged by the state of dating. There is less effort, less faithfulness, less value seemingly being put on having a happy, healthy relationship. But just because it’s rare doesn’t mean it’s nonexistent.

Always remember: Stay strong, stay positive, and stay true to yourself. The right person will love everything about you that the wrong people took for granted.


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  1. rlcarterrn on May 2, 2016 at 9:38 am

    Very interesting article! It is easy as a woman to think we have it harder b/c we’re always having to think about staying safe & not putting ourselves in bad situations, etc. But when I really think about it I don’t envy guys either b/c you are so right when you say that being the one who is expected to make the first move is not easy. I can’t imagine how intimidating that must be.

  2. TonyT on May 2, 2016 at 12:19 pm


    This is such a great article. You are so right and you have hit the nail right on its head. Just the other day I was saying the same thing that dating is expensive, exhausting (sometimes I just want to stay home but…), however it is worth it. I am learning so much…The journey, although bumpy at times is worth it and with God’s help we can make it. Continue writing great articles…God bless.

  3. Tim on May 3, 2016 at 3:42 pm

    “I understand that there seems to be a severe lack of decent, genuine men walking the earth these days – though I do believe they are still out there.” I DON’T understand James, are you saying there is a shortage, or just that it seems that way?

  4. Simo El Abbadi on May 8, 2016 at 6:47 pm

    a smart friend, lol.

  5. Bill on May 21, 2016 at 11:57 pm

    Thats why you have a steady girlfriend and then when you have the energy you date on the side. Get the best of both worlds.

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