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Dating Tips for New Entrepreneurs and Night Owls

You've got dating questions. Our expert has answers.

GREY Journal

Who is Alex and what is this? This is an advice column where I, Alex, answer your questions about dating and about life. Got a question you want to see featured? Submit it in the comments below!

Dating for New Business Owners

“I am in the process of starting my own business and a lot of my money is tied up in that right now. I still want to date, but I can’t afford to take my dates anywhere impressive. What should I do?”

Anyone can take a date to a fancy restaurant or trendy bar. And there’s definitely a reason people choose to go on dates in these places. Alcohol, good lighting, welcoming atmosphere—those all do a lot to facilitate conversation and frame one in a positive way. But you don’t actually need expensive cocktails and flattering lighting to make a date great. You just need to be creative.

Do you have a dog? Invite your date to come on a walk with you and your dog. People love dogs. Or meet for coffee instead of drinks. It’s cheaper and it’ll probably fit better into that busy business-building schedule of yours.  Dead set on dinner? Ask your friends or scour the internet for a cool hole-in-the-wall. The important thing is finding unique things to do that represent your personality and keep your date engaged while hanging out with you. Be memorable. Be interesting. And spend some time getting to know your city. Finally, as you all know, I am a huge advocate for warm whiskey from a paper bag in the park. Seriously. I just like being outside.

Dating When Working Nightshifts

“I’m a baker. I pretty much need to go to bed by like 7pm every night so I can be up in time for work. How am I supposed to date when I go to bed before most people even get dressed to go out?”

There are some people that like to get up early. Now, I personally can’t stand getting up early so I’m really not entirely sure where you’d meet one of these types of people. But they exist! If you go on dates with people who like going out at 11pm, you’ll end up in a relationship with someone who likes going out at 11pm and then you’ll both be miserable.

So here’s my suggestion: figure out something that people who like to get up early do and get into—and possibly involved in—that. Some people like to go for bike rides early in the morning or go fishing or bird watching or take long exposure photographs of landscapes. Get into something and either join a group for people who do it or (bare minimum) list it as a hobby in your bio on tinder (with some dope pics of you doing it, obviously).

Now, instead of meeting people that spend their Saturday mornings either at an after party or sleeping off a hangover, you’ll meet people who are interested in spending time doing the thing that you’re doing at that time.  Also: Coffee and/or brunch dates, they’re a thing. It’s 2019, we day drink on the weekends now.

Have a question for Alex, our dating expert? Visit his blog Ask Jeff’s Dad or leave a comment down below!

Alex Stone
Alex H Stone and his cat Jeff live in Minneapolis, MN. Alex H Stone has an MFA in Creative Writing. In his free time he enjoys taking pictures and sneaking into places he shouldn’t sneak into—but don’t tell anyone. For more Ask Jeff’s Dad, visit us on the web at www.askjeffsdad.com

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