Tina Tessina
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dating 2 guys

Many singles want to ensure they’re finding the right person to build their life with, and, in this busy day and age, that can equate to dating multiple people at a time. More and more individuals are looking at new ways to find love and optimize their chances of finding someone they can spend the rest of their life with. You may be having a hard time choosing between two people, want to explore all options fully or want to experience more of your local dating scene. Whatever reason, we provide useful advice alongside some of the benefits and problems that come from dating two men at once.

How to Date Two Guys at the Same Time

For singles who haven’t done this before, being in a relationship with multiple guys at a time can be a challenging task. There is a lot to organize and keep track of when dating multiple men, such as big life events, conversations, and their interests. The ways you can effectively date two men at once include:

  • Being organized and proactive. You may lose a bit of spontaneity, but keeping track of dates and organizing your time together more effectively will help.
  • Try to create diverse and unique experiences with both of them. If you do the same things with both men, it is more likely that you will have trouble remembering what conversations you had with who.
  • Being honest about the fact that you are dating two people at once can eliminate a lot of stress and problems.
  • Don’t spend too long in a relationship with two guys as it is unfair to keep them both hooked. Be honest with yourself about who you can genuinely see a future with. It doesn’t take as long as people think to discover whether you can go further with someone relationally.
  • Fully engage with what both men are sharing with you and honestly think about them as people.

Ideas for Dating Two People at Once

Now that we have explored how it is prudent to discuss ideas for a relationship with two guys at once, such as where to go, how to approach your dates and where to take them.

  1. Going to generic restaurants and coffee shops isn’t going to work with creating unique and memorable experiences. Instead, have dates where you’re crafting something together, taking classes or volunteering. These form unforgettable memories and reveal more about the person you’re dating.
  2. Hold off on too much physical intimacy before deciding who you want to get to know further. This will prevent you from forming a bond with someone who you may end-up not dating further.
  3. Avoid going to the same place you have taken the other guy or forming a similar experience you had with the other as it seems impersonal and can impact how separate you keep the two dating lives.
  4. Weigh up what you like about both of them and see what one fits more into your life goals and your values. That doesn’t mean that you compare them against one another but understand what you need from a partnership with someone.

Dating Two Guys: Pros & Cons

As with anything, there are pros and cons to seeing two men at once. Singles who’re thinking about dating multiple guys at once should weigh-up these benefits and issues before starting to date.


  • Provides more time to decide who is right for you
  • Can explore multiple options at once
  • Dating life is vivid and diverse
  • Form genuine connections in shorter periods
  • Explore different kinds of relationships


  • Can feel dishonest and that you’re hiding something
  • Lead into comparing the two people
  • Difficult to keep track of what you did with who
  • Can become stressful

It depends on what kind of person you are and the situation itself to fully explore the pros and cons of each. It is always best to be honest about what you’re doing and why to the people you want to date, as this can prevent a lot of pain. It is wise to take every situation as it comes, and in the earlier days of dating, it isn’t as difficult seeing two men at once. However, singles who start to get into deeper relationships and continue to date multiple people have a hard time and maintaining the relationships they’ve built.

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