I Think My Friend's 'Limousine Strategy' Is Crazy!

By Dr. Robert Wallace

October 1, 2026 6 min read

DR. WALLACE: I'm a male college student, and one of my good friends is a guy who has a very interesting strategy when it comes to dating. Every single time he asks a girl out on a first date, he'll hire a limo, pick her up and take her out to dinner, a concert or whatever event they are attending. He does this only on the first date, and when I asked him why he does it, his reply was that he wants to always make a good first impression.

The interesting thing is that he has a part-time job and a little money but definitely not a lot. Therefore, when he spends money on a limo, he has to really budget his funds to be able to pull this off, but I've seen him do it four or five times already.

Do you think there's something wrong with my friend? Do you think he has some kind of psychological problem because he has to use a limo every time he asks a girl out on a first date? — I Think He's Crazy, via email

I THINK HE'S CRAZY: My viewpoint is that this is an interesting and innovative strategy when it comes to dating. I don't see that there's anything wrong with it at all, as it's not like he's using a limo for every single date. People have different ways they like to make a good first impression, and he certainly found his own unique way of doing so. Hopefully he's savvy enough to have struck a deal with a local limo service for a volume discount.

In addition, knowing he's going to spend money on a limo in advance may actually have advantages for him. It might make him much more selective in who he asks out on a first date rather than just randomly accumulating dates the way some guys do. Overall, I tip my cap to him for coming up with his own strategy, funding it himself, and then going on from there without acting like he has more funds than he actually has. In fact, once his dates understand that he's a guy of modest means, they may be even more impressed that he invested in their first date to get the potential relationship or friendship off to the best possible start from his perspective.

WHY DO MY PROBLEMS SEEM TO ALWAYS COME IN BUNCHES?

DR. WALLACE: I'm a very busy college student, the way that most of us are these days. There never seems to be enough time to do everything I'd like to do, and life seems to fly by quickly each day, week and month.

Over the past year, I've noticed something very interesting. There will be times that my life will cruise along with its usual busy modality, but it'll progress relatively smoothly for several months in a row. Then seemingly out of nowhere, all of a sudden, I'll run into a problem in one area of my life, and before I can even begin to start solving it, another one springs up in another area. Then when I have two difficult situations to sort out, a third and sometimes even a fourth will descend upon me! What is up with this? I've had this yin and yang experience where I've gone through several months of smoothness and then a rogue two or three weeks of multiple disasters. Why does life persist in hammering me so hard from so many directions at once sometimes? — Ups and Downs Are Tough to Deal With, via email

UPS AND DOWNS ARE TOUGH TO DEAL WITH: It's often been said that life is a never-ending series of random, unpredictable events. As human beings, we often crave structure, routines and orderliness. But that's not how life always works, as your experiences clearly delineate.

Unplanned occurrences, happenings or experiences are going to happen from time to time, and the nature of randomness means that they will occasionally come in bunches. I think over a longer sample size, you'll have fewer experiences of so many difficulties at once, but it's entirely possible to happen to any of us at any time.

At the very least, while you are perhaps young and strong, you're learning to deal with setbacks and difficulties at this phase of your life. Hopefully you're battling through them well, making the best possible decisions and banking these experiences to lean upon down the road in your future.

I personally often see a useful key to a difficult situation as taking stock of it. By this, I mean that once something has happened or occurred, spend only a minimal time in frustration, denial or wondering why it happened. Then as quickly as possible, shift your mental focus to a pragmatic mode. Think about what needs to be done quickly or early on once something difficult arises. Also realize that many problems don't need to be solved all at once, but making a thoughtful and correct first step early on can truly bring big benefits as you wade through the difficulty to a resolution.

Do this especially when troubles come in bunches. Don't try to solve one entirely at first before you deal with the others. Deal with each one in this similar manner at the opening stage, and then as you move through each, solve them in the order of importance to you (or in order of ease or difficulty of working through them). Remember to lean on the help of friends, family and others when necessary and appropriate, and always stay strategic.

Finally, if some of these things will reflect negatively upon you, contact the people who will be affected early on even as you're dealing with the situation so that they can be aware of what's happening at the very least. You may be surprised that some people will provide you a modicum of grace, and some may even roll up their sleeves and help you deal with something that affects you both.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at [email protected]. To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.

Photo credit: Richard R at Unsplash

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