“I’m dating lots of men and don’t know how best to manage it.”

I’ve been dating someone for four months. He says we aren’t exclusive, and so I’m still dating others, but now I have a problem. A man I’ve been writing wants to come into town to see me, and even one of my exes has come back. It’s very exhausting to be talking, investing, and sharing myself with more than one man every day.  My past dating history is that I always dated one man at a time.  Honestly, I feel like I’m cheating on the guy I’ve been dating for four months although my girlfriends tell me I’m not.

Q #1—Do you have any ideas or techniques on how I can “subtly query” the guy I’ve been dating for four months to find out what’s going on with the changes he’s making and why?

A—I would touch him on the arm and say to him at the end of a date, “I’m really struggling. I want you to know I’m more of a one-man woman, but until someone asks me to be exclusive, I know I need to keep dating others. It’s hard for me to share my feelings and needs with more than one man at a time, and of all the men I’m dating, I’d rather move forward with being exclusive with you. Let me know if you want to discuss the idea of becoming exclusive. I really think you’re great.” Then I would kiss him sweetly or give him a warm hug and walk away. First off, if the relationship has not progressed toward kissing, I think it should. The longer you wait, the longer you both may doubt the relationship and the potential connection or chemistry you feel or could feel.

Q #2—This guy I’ve been dating for four months appears to be afraid of commitment.  If so, and if I love him, what’s a wise amount of time to invest/dedicate to this relationship before I stop?

A—You need to pray and follow your conscience on this one, but, in general, if you use the statement above and he doesn’t bring up being exclusive and/or you don’t kiss within the next month, I would end the relationship. It’s going nowhere. Oh, and when I encourage you to move forward with kissing, this is with the understanding that you are only kissing one man out of the men you are dating.

Q #3—The MOST important question.  The “old flame” with whom I’ve reconnected led me on for 5 years. He said he loved me and then later said he never did.  How, then, can I tell if a man DOES love me???  If the way a man treats you, responds to you, and his use of the words “I love you” don’t certify that he does love you, what does??? Now that he’s back, some of the confidence in dating I’ve acquired in the last year and a half has dissipated; I’m worried that I won’t know if a man really loves me.

A—A man’s actions should expose the truth of what he really feels. Thus, a man who acts like he really wants to be with you probably does. Relative to your ex, the effect he’s had on your confidence since he’s come back in your life says it all. I am disturbed by the fact that he drug out the relationship with little regard for your feelings (i.e., empathy), but the fact that your feelings and confidence have so quickly become negatively affected tells me he is emotionally immature. I suggest you end contact and be firm about it. If he can, he will string you along again. Run.

I hope this helps.

Good luck,


3 thoughts on ““I’m dating lots of men and don’t know how best to manage it.”

  • “Oh, and when I encourage you to move forward with kissing, this is with the understanding that you are only kissing one man out of the men you are dating.”

    Can you expound on this a little bit, or does your book cover this? Do you mean even a quick kiss at the end of a date, or something else? I was thinking that I had read that your advice to men is to kiss a woman by the 4th-6th date. If she’s dating several men for 6-8 weeks or more, there could be some overlap there.

    You have talked a lot about continuing to date others, but here you seem to encourage more of a one-at-a-time approach. Is that specifically tailored to the woman asking the question, since it’s difficult for her to date several, or do you feel that one at a time is ideal?

    • Good question. In general, if you are kissing a man or woman and they don’t know that you are kissing others, they may feel betrayed. So it is best to only kiss one man or woman of all the people you are dating unless you clarify how the other person feels about you giving simple affection to others.

      In general all kissing should be kept simple or you will run the risk of sexual contact and over complicate the relationship, which increases the risk of rejection.

      Since I encourage singles to date more than one person for the first six weeks of dating, I also encourage them to clarify to those that they aren’t comfortable kissing yet that they go slow in this regard.

      I encourage men to kiss only those women that are on the A List between the fourth and sixth week, otherwise she will begin to doubt their interest in her and their confidence. They shouldn’t kiss girls on their B List unless no one else is currently on their A List. In this way, they can discover if a possible chemistry may be developed after the kiss. If it isn’t they should stop seeing her after the sixth date. If they kept their affection simple, this should not unduly hurt the women.

      I hope this answers your question. Alisa

      • That does help, thanks! It kind of makes my brain hurt a little bit to try to remember all the ‘rules’ and guidelines! I wish we could just approach this naturally. I’m here though, because I want to be successful, so I’ll willing to take on the pain of learning to do it this way!

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