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You like dating multiple women and you like being in a relationship too? Don't listen to the naysayers - you can have your cake and eat it too, without a being a sleazeball, as long as you know what you're doing. Nick Savoy, a dating expert from Love Systems and creator of the Relationship Management DVD Course, is here to help!
Moral reasons aside, its dumb to lie about this. Most women are too good at sniffing out deception from a long-term partner, especially about infidelity. In the meantime, you'll drive yourself crazy keeping your stories straight. As Mark Twain wrote, "telling the truth means never having to remember what you said." Most women respect a man who is honest and up front about what he wants, even if it's not what she's used to hearing.
Some women will never date a man who isn't exclusive to her. Other women prefer open relationships. Look for women who are free-thinkers, who are either younger or older than the prime "must settle down and have children" years, and who are comfortable with themselves and not insecure. You don't need her to be fully enthused about the idea from Day 1, but there's no point if she's completely against the idea.
If you travel all the time, are always at different events, and are very social and always surrounded by people, then it "fits" that you could want or be used to a non-exclusive relationship. It doesn't mean she'll want this too, but the odds are much greater than if you seem to spend most of your free time at home. In other words, she's more likely to do an open relationship you come across more as a rockstar than an accountant.
Here's somewhere where a lot of guys mess up. They think that dating multiple women means spreading the same amount of attention over more people. No. Each relationship is separate. If anything, you need to be even more attentive, connected, and committed than otherwise. Even women who are OK with you dating others will be a lot less willing if they see that other women are cutting into time and attention that she expects with you.
Tell a story about something that happened when you were on a date. Make the story something funny that you'd tell anyway, but drop in a quick aside that you were in an open relationship at the time. Maybe she'll want to talk about this, or maybe she'll quietly consider it for a while. Either way, you've communicated that you've had non-exclusive relationships before and they worked for you. When the subject comes up later, it won't be a surprise.
This usually happens during the "what are we?" conversation when a dating situation turns into a relationship. Usually the woman will initiate this conversation. Sometimes, people just evolve into a relationship after dating for a while - don't let this happen, or you won't have "the talk" and she'll probably have default (monogamous) relationship expectations. Initiate the conversation yourself if you have to. This is when you come back to the idea of an open relationship.
Few women are going to agree to you seeing other women if they're not allowed to see other men. This is true even if she doesn't actually want to see other men (which can happen, depending on her personality and the relationship) - she'd still think it unfair if she you were allowed to and she wasn't. Speaking of which, most women are better at picking up men then vice versa, so if you don't think you can handle your girlfriend getting more action than you, this is a can of worms you should stay away from...
There have to be rules. Don't assume that she has the same expectations that you do. Or you risk a situation where, for example, she thinks kissing isn't OK but friends are fine, you think the opposite, and then you have a huge fight because you made out with a girl at a bar and she blew your friend. Define limits of who, what, when, how often, safety expectations, and what (if anything) you need to tell the other.
If I've seen this once with Love Systems clients, I've seen it a thousand times. Guy starts dating multiple women. Guy realizes to his shock that they are okay with this. Guy starts showing off, talking to one woman about another, letting them leave stuff all around his house, and keeps putting the situation in her face. Woman moves on. Absolutely crucial - don't ever embarrass her in front of her friends.
Most relationships change and adapt over time. Don't assume that because you had "the talk" once that you'll never have to revisit the issue again. It's a rare boyfriend who just randomly checks in to ask how his partner is feeling about everything and about the relationship (especially when he's happy about things, as opposed to trying to give himself cover to discuss his own concerns), but it will pay off in spades. Good luck!
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