It’s not uncommon to be attracted to more than one person at the same time. Whether or not you act on those feelings, won’t only affect you. If you want to date more than one person, make sure that everyone involved understands this and is okay with it. If you’re dating someone, and you haven’t talked about the rules of engagement (including how exclusive you will be), don’t assume that they’ll be okay with you dating someone else at the same time. Many people won’t like it. Tell any and all other partners what you’re up to.
It might seem awkward to have to admit to potential dates that you don’t actually want anything monogamous to bloom from your meetup, but it’s less awkward than having to tell them they’re actually just one relationship out of many when they hit you with a third-date “So, what are we?” According to Jessica O'Reilly, PhD, a sexologist and host of the podcast Sex With Dr. Jess. "Some people are more honest about their intentions from the onset, and they therefore have happier relationships — regardless of whether they date one or multiple people at a time," Dr. O'Reilly says.
If you’re worried someone on your roster will object to there being a roster, too damn bad. They have the right to be opposed and not be deceived. Once you have discussed what you want from your setup, you still have to check in to see how your partner is faring, and whether or not they're still satisfied with the arrangement, Dr. O'Reilly says. When you are juggling a few loose relationships, there's a tendency to just brush over the deep topics, and keep the conversations light — but that's not a very good strategy if you want to have sustainable relationships. "It's important that your communication is honest and includes expressions of vulnerability," she says.
If you’re not sure of how someone feels about you, ask them. Never make assumptions. If someone loves you, then they will want for you to be happy. You can’t force someone to accept, and be happy about something they really don’t like. I came across this blog called, A Conscious Rethink. It provided 17 rules to follow when dating multiple people…check them out:
1. Think about why you want to date multiple people
2. Be honest with everyone
3. Respect everyone’s privacy
4. Don’t turn it into a competition
5. Respect their choices
6. Don’t expect them to date only you
7. Know that a relationship is not a guarantee
8. Don’t date too many people
9. Know when to stop
10. Don’t feel guilty
11. Have a life outside of your love life
12. Don’t make things complicated with sex
13. Don’t play with anyone’s emotions
14. Be clear about what you want
15. Date separate people on separate days
16. Don’t share too much
17. Know that you can still fall in love
Since you have more dates lined up, there’s always hope for the next one to be better. If you have a lot of dating experience and you’ve learned a lot about yourself, you’ll learn what you really truly want out of a relationship. Once you know that, you’re set to find someone you can really make a life with.
I so agree that you have to know where you stand when dating. Just be up front from the beginning what it is that you desire and if you actually desire with that person because that can be misconstrued as well I've learned a lot over the last year and a half and so just be honest and forthcoming from the get-go and then hopefully no one is left dumb founded when someone moves on with someone else because you know you already knew up front that he or she was dating someone else as well.