I’ve traveled on business extensively for over 30 years, mostly by myself and have lost track of how many dinners I have had by myself. That said here are a few of my tips for how to combat eating alone.
Become friends with the restaurant owner or manager This is a pretty common one for me. Because of my excessive OCD I like going to the same places all the time. When I’m traveling on government contracts I usually stay in the same hotels and eat at the same restaurants. I tip well and the owners or managers of the restaurant start to notice “regular” customers. I have had the owner or manager actually sit down at the table with me and join me for dinner and even comp me a drink or dessert or something.
Become friends with the bartender I usually eat at the bar in the restaurant and sit at the same seat at the bar. More people are coming and going and eating alone isn’t as obvious as sitting at a table in the dining room. I tip well and the bartenders love me. If it’s not busy, like on a Monday night the bartender will chat with me the entire time I’m there.
Become friends with other businessmen also eating alone
I have met great contacts this way too. I typically pick a seat at the bar next to them or a couple seats away. I will then strike up a conversation and eventually exchange business cards. This usually leads to follow up opportunities.
Become friends with the most beautiful woman in the hotel lobby or bar The beautiful women never seem to get asked out and if they are at the hotel or restaurant bar then they are usually there for cheap drinks during happy hour so she is already 1–2 drinks into a good time. Sometimes we will just stay at the bar but other times, since I know the owners, we will move to a table in the dining room. I recall one time moving to the dining room with a stunning tall blonde and the rest of the dining room was paying attention. It was priceless. Only once did a woman say No and it was funny. I asked her if she would like to join me for dinner and she said “Dinner will be $400” to which I replied, “Nah, only if we get really expensive wine”. Unfortunately she wasn’t talking about the cost of the meal she was a high end escort and was actually negotiating her fee for dinner. I passed.
Become friends with a table full of fun people in the dining room that has 1 seat open Sometimes I will sit near them and strike up a conversation or the best way is to offer to buy them dinner if they move to another table. They typically will either accept or decline but usually will offer me to join them.
Become friends with yourself I often enjoyed just dining alone. It gives me time to think and plan.
Become friends with your to-do list I often bring a laptop or tablet and get work done.
Become friends with social media More often these days I just play on my phone or post to Quora or chat online with my online friends.