May 1, 2026
Upshot Dating®
Should I Date Other Men? When Dating Multiple Men Is (and Isn’t) the Right Choice

Upshot-Dating® can mean dating more than one man at a time (without being physically intimate), but Upshot-Dating® does not always imply you are dating multiple men.

Read here: What is Upshot-Dating®, the Modern Queen’s Way to Date

While my Signature System provides clear steps and solid, replicated, systematic guidelines with applicable terms and tools that have been replicated worldwide, it is ALSO highly adaptable to the individual clients I consult and work with.

One way Upshot-Dating® is highly adaptable is in dating one or more men simultaneously.

Contrary to random, less-than-expert advice tossed around on TikTok and the like, making such a decision first requires a closer look at three parameters: (1) what is going on inside you as a person, (2) your specific relationship situation, and (3) your relationship timeline.

When Dating Multiple Men Is The Right Choice 

Here is when it is the right thing to do and date more than one man at a time. When I opened my consulting business, I initially worked only with single ladies and helped them go from single to engaged. Due to an over-90% client retention rate, I also expanded my services to include consulting with women in relationships and marriages. If you are new to my system and in a relationship, it may or may not be the right thing to date multiple men simultaneously; I will address this later in the article.

For my first cohort, the fully single ladies, it is, of course, the right thing to date multiple men. This is the way to go when you are just starting to date as a single woman. It is the most logical, time-efficient, and proven way to date, if you are single and your goal (upshot) is to find the right man, want marriage, and start a family.

It also makes sense to start seeing other men if you are in the girlfriend trap.

Read my full article here: What is the Girlfriend Trap?

When Dating Multiple Men Isn’t The Right Choice 

Here is when it is not right to just go out and start dating others. According to social media, “date others” and “break up” seem to be the standard replies to any relationship issue.

Simply going out to date other men without considering your situation can ruin a relationship that would have worked if the real issues had been addressed.

So, please do not just date others and use it as an escape; if the right thing to do is to face what is going on, learn and improve your relationship.

Case Studies: 

Here are two private client examples where “just date others” as a quick fix would have been wrong.

Alba became my client when she was already in a committed, mostly happy relationship. She wanted to work on her past because her previous marriage caused some unproductive patterns in her current relationship. Alba was worried that I would ask her to date others, which she clearly did not want. She trusted her partner and knew their relationship would lead to what she wanted. When she was 5 months pregnant, he proposed. In Alba’s case, there was no need to date others; instead, we focused on her doing this work for her own healing.

Sheila had an unhealthy, at times toxic, dynamic with her boyfriend of three years, with lots of drama and jealousy. She almost started dating others after watching TikTok. Luckily, she knew better and consulted with an expert first. I made her see that, in her case, she was avoiding a deeper issue and would only further fuel the already-burning fire. We worked on things on her end, and after a few months, her relationship dynamic was completely changed, and her boyfriend proposed to her.

Conclusion
  • If you are single and set out to find the right man fast, you are starting on a clean slate. Of course, date more than one man.
  • If you are in the girlfriend trap, it also makes sense to start dating more than one man.
  • If you are in a relationship where you are happy with how things are, feel safe, and trust that he will propose, like Alba was. Of course, do not destroy that by suddenly dating other men.
  • Do not revert to dating others as a form of control; try to make him propose, push him to be jealous, or avoid a deeper issue, as TikTok suggested Sheila should. Instead, address those issues so that you will be able to see if he is the right man for you.

If you are still unsure and would like me to assess your situation, you can schedule a call with me here.

Book a 30-minute Assessment Call 

Dedicated to Your Success in Love Since 2016

Anina Green | Soulmate Katalyst Ltd.

Clinical Psychologist, Certified Dating Coach, Wife, Physicist, Founder of Upshot-Dating®

Find further reading on the topic here: 

Testwifing™: a Strategic Error – Why Being a “Forever Girlfriend” is a Trap

The Girlfriend Trap: 3 Signs You Are in It and 4 Strategic Steps to Get Out

When Being a Girlfriend Makes Sense — and When It Doesn’t

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