General Dating Questions/Who Should Pursue Him?


My roommate and I are good friends and get along well. However, recently we have both fallen for the same mutual friend. We have both been texting, flirting, and hanging out one on one with him, and he has expressed some form of interest in either of us at a given time. She has expressed to others that she is interested in him, which is something I have not done, largely due to the fact that I know that she really does like him and I don't want to seem like I am encroaching on her "territory". My question is, what would be the best way to go about deciding who should pursue him?

Hello Maggie!

This is a really great question - one that comes up all the time but is rarely asked.

There are two ways to look at this: 1) who got there first and 2) who has the best chance.

I see this more often in guys where a couple of friends target a particular woman. Many times, it's the guy with the least possible chance that makes the first move. By doing so, he kills off the chance of the other guy! This is something you have to work out up front because if you don't, those guys won't stay friends (or "hunting partners") very long.

At least you're asking before anything begins happening.

Let's deal with the second issue first. Between you and your friend, whom do you feel has the best chance with him? This may be difficult to answer at first, but consider who is the best match - on many levels. If you can see these likely, so can he.

Of course, if your friend is telling everyone that she's interested in the guy and is pursuing him, she got there "first" and will start dating him or get blown out of the water. By the way; this is another tactic many people use to "mark territory". They don't actually pursue the person they're interested in. Instead, they let everyone know that they're interested so that if someone else in the group goes after that person, they'll look bad to everyone else. This is just as bad as the (previous) guy who jumps in front of the parade!

You and your friend should talk about this. You make your case and she makes hers. Based on that discussion you can decide to work together to help that person succeed. Then, the next time, that person helps the other one. This is a way to not only keep the friendship solid but to make sure everyone gets to play.

Of course, the guy has a choice here too and isn't likely to go after the other one if the first doesn't work out. Besides, would you want to be someone's second choice? Of course not.

Best regards...

Dr. Dennis W. Neder
CEO/Executive Producer
BAM! Productions
Remington Publications
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”

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Dr. Dennis W. Neder


I'm able to answer any sort of question related to the approach, meeting people, dating, sex, relationships, break-ups, non-legal marriage and divorce questions, and anything in between. I've helped over 30,000 people with their individual issues. IMPORTANT: Please, PLEASE don't ask me, "what was he thinking..." or "why did he say..." types of questions! I DO NOT READ MINDS! There are 1,001 reasons why someone does what they do, says what they say or thinks what they think. If you *REALLY* want to know what they were thinking, saying or why they were acting that way - go ask them! Be sure to check out my FAQ's on my website at: You can email me directly at:


I am the author of the books "Being a Man in a Woman`s World I & II" and "1001 Places and Techniques to Meet Great Women" and 11 others. I`ve spent the last 20 years studying the art and science of every aspect of relationships, and have answered over 30,000 letters from readers all over the world. My main focus is men`s relationships with women, but I also have many female readers and answer questions for them regularly as well.

Doctor of Philosophy

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