How to Date an Entrepreneur

Co-authored by John Keegan

Last Updated: February 13, 2023 References

Dating an entrepreneur is a unique experience. It can be thrilling to date someone with their own sense of independence, curiosity, and resolve. There are some unique challenges that come with the relationship, however. Making plans can be difficult and you often end up coming in second place to work. With a little effort, you can make your relationship work.

Method 1

Method 1 of 3:

Making Time for One Another

1
Check their schedule frequently when making plans. An entrepreneur does not work a traditional 9 to 5 schedule. When it comes to making plans, ask about their schedule frequently. They may be free at odd hours, so dinner and a movie Saturday night is not always feasible. You may end up meeting for lunch on a Wednesday afternoon instead.^{[1]
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2
Make plans close to the day. Do not make plans too far in advance, as an entrepreneur's schedule is subject to change. If you make plans a week in advance or more, it's likely your date will not be able to make it. Try making plans a couple of days in advance instead of a couple of weeks.
- If there's something you really want to do that requires advanced planning, like going to a concert, take someone a friend instead.
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3
Indulge their new hobbies and whims. Entrepreneurs are curious by nature and always want to try new things. As they're frequently distracted by work and new pursuits, you can spend time with an entrepreneur by engaging in their new hobbies.^{[2]
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- For example, if your significant other wants to start gardening as they're looking to branch out their business into agriculture, join in. The two of you can make a garden together so you can spend time together as a couple.
4
Account for long work hours when making plans. An entrepreneur may work very long hours. It's not uncommon for workdays to be 10 hours long instead of eight. Make plans that don't take up a lot of time. For example, plan to spend half an hour cuddling and watching television before bed instead of planning a long, elaborate evening.^{[3]
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- You can also plan for brief meetings in between your partner's schedule. For example, plan to meet for a quick cup of coffee in between your partner's meetings with clients.
5
Find inexpensive ways to have fun. If an entrepreneur is just getting started, money is usually an issue. Their budget will be tight as they'll be pouring a lot of their own income into their business venture. Inexpensive activities are generally preferred.^{[4]
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- Look for free events in your area, like free concerts and shows.
- Plan to spend time at home. Have a BYOB game night with friends instead of going out for drinks.
6
Make backup plans. Expect an entrepreneur to back out of plans at the last minute. Emergencies at work and unexpected obligations are common. When planning a date night, always have a backup plan in case your significant other can't make it.^{[5]
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- It can help to plan get togethers with your significant other and mutual friends. This way, if your partner backs out, you'll still be able to get out.

Method 2

Method 2 of 3:

Handling their Emotional Needs

1
Expect some emotional ups and downs. Entrepreneurs are passionate by nature and tend to have extreme emotional ups and downs. It's not uncommon for an entrepreneur to go from happy to frustrated in a few minutes. Learn to anticipate changes in mood.^{[6]
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- Adopt the mantra, "This too shall pass." If your partner is moody and it's frustrating you, remember how quickly their mood can shift. Even if they're getting on your nerves now, the switch will flip eventually.
2
Encourage them to take breaks. Entrepreneurs have a tendency to push themselves too hard. A great way to provide support is to remind them to take breaks. Let your entrepreneur significant other know when they're pushing themselves too hard and offer a diversion.^{[7]
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- For example, say something like, "I think some space may help you get perspective so you can deal with this issue more easily. Why don't we watch a movie and have something to eat and then you can go back to work?"
3
Let them express their opinions. Entrepreneurs are opinionated by nature. If you don't enjoy debating things like politics, you won't like dating an entrepreneur. They're bound to have opinions on current events and enjoy being able to express them.
- You don't have to agree with an entrepreneur. In fact, entrepreneurs love a good debate, so share your opinions as well.
4
Be supportive during periods of self doubt. Self doubt is common with an entrepreneur. When you're in a business prone to many failures, you're bound to doubt yourself at times. You can help by encouraging your partner when they feel bad about themselves.^{[8]
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- Remind them of their successes when they feel down. After a setback, emphasize how far they've come and how much they've accomplished.
- Talk about the qualities about them you admire. For example, "I know you're disappointed that deal fell through, but it took so much grit to even pursue it to begin with. I love how much courage you have."
5
Give them space. Entrepreneurs are independent by nature and need a lot of space. If they seem quiet and standoffish, they probably need some time to themselves. Find activities you enjoy doing alone, like reading or watching television, that you can engage in when your partner wants space.^{[9]
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Method 3

Method 3 of 3:

Sustaining the Relationship

1
Try to keep up with an entrepreneur. The great thing about dating an entrepreneur is that their motivation can rub off on you. Entrepreneurs dislike laziness, so try to keep up with their spirit of determination and innovation.^{[10]
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- Take classes and try new things. If you've always wanted to learn to cook, for example, try taking a cooking class and hosting dinner parties more often.
- Not only will doing your own thing keep an entrepreneur interested, it will also keep you busy while they're running their business.
2
Decide if you can accept occasionally being second place. Not everyone is able to date an entrepreneur long term. You will sometimes come second place to their business. Ask yourself whether you can deal with your partner occasionally missing out on big occasions because their business demands it.^{[12]
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Cope with a semi long distance relationship. Entrepreneurs travel a lot. If you can't handle sleeping alone, a relationship with an entrepreneur may not be right for you. Learn ways to cope emotionally while your partner is away.^{[13]
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- Communicate from a distance as this can help you feel more secure in the relationship. Call one another each night and do things like video chatting.
- Try to engage in activities together from a distance. For example, you can both read the same book or watch a movie at the same time while texting each other comments.
4
Don't forget that this person cares about you. Entrepreneurs are sometimes lost in their business, but that doesn’t mean they don’t care about you. Remind yourself an entrepreneur is with you because they like you. Even if their business demands a lot of their time, it doesn't mean they don't love and need personal relationships.