How to Have Two Boyfriends at Once

Last Updated: May 30, 2022

There are a variety of reasons why you might be curious about how to manage having two boyfriends at once. You may be polyamorous a sexual preference that translates as "many loves" and involves openly maintaining relationships with more than one romantic partner. ^{[1]
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Research source} You might be seeking non-exclusive relationships that allow you to test the waters of dating without making a serious commitment. You may, on the other hand, be attempting to maintain two boyfriends in secret. If this is the case, you should be aware that doing so may undermine both relationships and damage the possibility of a meaningful future with either romantic partner. There are many good arguments in favor of dating multiple people. Maintaining two "boyfriend" relationships when each of your partners believes your relationship is exclusive sends you into considerably murkier moral territory.

Part 1

Part 1 of 4:

Dating Two People on a Non-Exclusive Basis

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Use non-exclusive dating relationships to explore. Dating two or more people can reap a variety of benefits for both you and your potential romantic partners.
- Interacting with more people at the same time may speed up the process of finding the right person.
- Dating two people allows you to compare and contrast individuals and personalities. You may learn important lessons about your own personality and preferences.
- You will hone your first-date skills and may boost your self-confidence. The more you experiment with dating, the more you may find you can move past your own nerves and take an analytical approach about whether your date is a good fit for you.
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Tell your dates you aren't seeking an exclusive relationship. (At least, not yet!) Honesty allows you both to thoughtfully evaluate your suitability for each other. You may find, too, that this has the attractive side benefit of arousing your dates' competitive instincts.

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Take your time. Don't rush into a relationship you'll later regret. If you've taken the opportunity non-exclusive dating provides to learn more about your self, your preferences, and your priorities, you'll make better decisions when you do decide it's time for a more serious relationship.

Part 2

Part 2 of 4:

Embarking Upon Two "Boyfriend" Relationships

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Determine your motivation. Do you view having two boyfriends as "cheating"? If so, recognize you will be living in moral tension. If you believe you are polyamorous, on the other hand, you may be seeking relationships that will be a better fit for your personal identity. ^{[3]
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Decide whether your boyfriends will know about each other. Perhaps you and they will find a polyamorous relationship satisfying. Even if your boyfriends are not themselves interested in multiple romantic relationships, they may find your honesty refreshing if you truly aren't ready to settle down with one person exclusively.^{[5]
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Establish your expectations for the two relationships. Do these boyfriends meet different needs? How will you organize your time and energy?
- Consider scheduling. When will you see each boyfriend, and for what types of activities?
- If you are keeping the two relationships secret, how will you ensure that one does not learn about the other, or vice versa?
- Think about how your other relationships may be impacted by having two boyfriends. Will friends and/or family approve? Who should you be telling? How will you cope with the possibility of appearing linked with one partner for some friends or relatives, and another for a different set?

Part 3

Part 3 of 4:

Managing Two Boyfriends

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Determine your strategy for maintaining each relationship. The scheduling considerations mentioned above will require constant maintenance if you are to keep your relationships with both boyfriends happy. This is a factor regardless of whether your relationships are open or secretive.
- Consider how you'll devote the time necessary to keeping up with your boyfriends' lives and needs. Doing so requires both time management and mental management to ensure you're keeping the details of each relationship straight.
- Compartmentalizing each relationship may be useful in keeping the two relationships straight. One boyfriend, for example, might be your running partner and tennis buddy, while the other is your go-to guy for homework sessions or coffee shop conversations.^{[6]
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Decide what you'll do if you encounter one boyfriend while spending time with the other. If your relationships are open, this question may be moot. If you are keeping the relationships secret, you'll need contingency plans.
- You may be able to camouflage the nature of your relationship by treating each boyfriend as a "friend." Consider the likely response from each boyfriend. Will they become confused or upset by your sudden lack of affection?
- Be aware that you may quickly become entangled in a complex web of lies and evasions. Quick thinking will be necessary and your moral discomfort will likely grow even more complex.
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Decide how you'll handle social events. Which boyfriend will accompany you to events such as weddings, the company holiday party, or other social events? The context in which you know each boyfriend may help answer some of these questions naturally, but in other cases you may find you need to choose.
- If you aren't prepared for a group of friends or relatives to identify one partner as your official "boyfriend," you may consider attending functions alone.
- Think carefully about your circle of relationships. Will selecting one partner to attend a given social function commit you to include him in the future? Will you run into trouble if overlapping social circles see you romantically linked with two different people?
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Decide how you'll handle social media. Even if you refrain from mentioning either relationship online, chances are high that you'll find yourself linked with one of your partners on a friend or relative's social media account. If your boyfriends know about each other this will pose fewer problems, though you should still be aware that jealousy could arise if it looks as though you spend more time with one than the other. If your boyfriends believe your relationship is exclusive you may find yourself with some serious explaining to do.
- Prepare for the possibility that your boyfriends will want to share news of your relationship with their friends and loved ones via social media. If they don't think they're sharing your time and affections, how will you handle this issue?
- Consider strengthening the privacy protections on your account so third party connections cannot readily access information posted by friends in different circles of acquaintance.
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Schedule time for yourself. One committed relationship can keep a person busy; two will likely have you running, especially if each boyfriend believes they are your sole romantic commitment. Contemplate what activities you find most restorative, and then ensure you leave some time in your daily or weekly routine to engage in these activities.

Part 4

Part 4 of 4:

Keeping Yourself (and Your Boyfriends) Safe

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Use proper protection if your relationships are sexual. Even if you only intend to engage in a sexual relationship with one boyfriend, prepare for the possibility that temptation may overcome your intentions in the heat of the moment.
- Remember that not all contraceptives prevent sexually transmitted diseases (STD). You owe it to yourself and to your boyfriends to ensure that everyone remains healthy. Always, always use a condom.
- Schedule regular physical exams as an additional safeguard.
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Know when you need to tell. Never place your partners' physical health in jeopardy. If you discover you've contracted an STD, your partners need to know even if it means spilling the beans to one about the existence of the other.
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Recognize that secrecy may also strain your mental and emotional health. The human brain is wired to tell the truth. Secrets especially those we perceive as negative can stress the part of the brain charged with sharing information. To cope with this burden your brain produces stress hormones that can impact your memory, blood pressure, gastrointestinal tract and metabolism.^{[7]
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Warnings

Secretly maintaining two "exclusive" relationships seriously jeopardizes your chances of ever transitioning to an exclusive relationship with one of these partners. Discovery of your past could make it very difficult for him to trust you in the future.

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