"I don't really consider myself a player," says 25-year-old Rob. "I date a lot."
Rob's friend, Seth, disagrees. "Rob is definitely a player. If you were to look up player in the dictionary, Rob would be in parentheses," he says with a laugh.
Rob lives in Huntington Beach, California where, he says, he has an exciting life. "I've been very successful at work, so a lot of guys look up at me and think, wow, he's got so much going for him, and yet I'm missing something. I've juggled many women, like, four or five at once. Yeah, it's tough. It's like a full-time job. I'm texting. I'm e-mailing. I'm talking on the phone. It gets crazy." But Rob says he wouldn't apply the term player to himself. "I thought every other guy does that, right? Most guys probably would love this problem, but I want to settle down. I've been doing this for like seven years. I'm tired of it. I'm having a lot of fun, but I'd rather have it with one person."
Seth reveals, "Rob probably has met the right woman about six times, but they've all blown right past him because he doesn't treat them right."
"I purposely date dumb women," Rob says. "I hate to say that. It seems like all the smart women drop me fast. I'm actually hoping Dr. Phil will at least coach me on how to find the right girl. That's my question. How do I make those smart girls come to me?"
Ana is one of the women Rob dates. She met him online and says he's the perfect catch. "Initially what attracted me was his looks. Because I live in Boston and Rob lives in Southern California, starting a relationship would really be challenging for us. We talked a lot, we e-mailed back and forth, and then he flew all the way across the country to see me."
She continues, "When I went to Southern California, it was as if time hadn't passed. He always has fun things planned to do, and he always makes you feel very special.
Dr. Phil asks Rob about Ana.
"She definitely is dating material," says Rob with some apparent reservation.
Dr. Phil reminds him, "You said, and I quote, 'I'm not that into her, but the sex is good, so why not?'" Rob shifts in his seat and gulps nervously. "Ana believes the only thing standing between the two of you is geography." Rob agrees. "And you know better. If she moved out here tomorrow, you would freak," says Dr. Phil. Rob agrees again.
"I told you this whole conversation we're having is a test, and you're saying, 'I want to change this.'" says Dr. Phil. "The change can start now. However many women you're involved with now, you can start by being straight-up honest with every one, instead of putting yourself first. You've got to get to a point where you say, 'I'm willing to tell the truth.'"
When Ana heard that Rob was talking to Dr. Phil and considering settling down, she jumped on a plane to Los Angeles. Dr. Phil sits down for a talk with her.
"Rob and I are dating. He's a very caring and sweet guy," she says. "He's real, he's down to earth, he's sensitive, he never misleads me into thinking something that's not real."
"Are you in love with him?" asks Dr. Phil.
"I am," she confirms.
"And if you guys were in the same town, same place, then this relationship would certainly go to the next level."
"Right," she says confidently. Ana says she would love to be married to Rob and have children. She says if he asked her to marry him, she'd say yes.
"Why do you get emotional when you talk about him?" he asks.
"Because it touches my heart," she says. "I have a lot invested in this relationship ... my feelings. I've made myself very vulnerable, but I think that's the only way to do it, to find love."
"I would prefer to know," says Ana.
"Is he involved with somebody else now, as far as you know?" asks Dr. Phil. When Ana says no, he tells her, "I want you to meet some women, because I want you to know the truth." He calls out to another room, "Ladies, come in. I want you all to meet Ana."
Two women enter, and Dr. Phil introduces them as Veronica, and Mai-Lan. He says to Veronica, "You know we have a project we're working on: Rob."
Mai-Lan confirms that she used to date him, while Veronica reveals that she's pretty seriously involved with him right now. Rob has even told her about Ana, and Dr. Phil asks what specifically he told her.
"He said that he used to date her," she says.
"Nope," she says.
"OK. But he was with you Friday night and he was with you Saturday night," he points out.
Next, Dr. Phil shows all three women a videotape of excerpts taken from Rob's interview.
On the tape Rob says, "I feel like the women that I date are just kind of dumb. I purposely date dumb women. I've definitely lied to get women in bed. I mean, who hasn't? When I'm dating a lot of women, I don't necessarily always tell them.
"I believe he just doesn't know what he wants," says Veronica.
"I think his actions are unforgivable," says Ana. "Anyone who acts that way obviously knows what he wants because he has gone to a lot of effort, fooling us."
"Here's the thing: all three of y'all are beautiful, intelligent, young, vibrant, energetic women. How is he doing this?" asks Dr. Phil.
"Well, Dr. Phil, I don't know. I don't know who he is any more," says Ana.
Dr. Phil invites Rob into the room with the three women. "What did you want to say?" he asks Ana.
"I don't have anything to say right now," Ana says bitterly.
"Ana, what's wrong?" Rob asks.
"You're a liar," she tells him. When he issues a denial, Ana says, "I just saw you on tape, what you said about me, that you directly told me that you can't date me?"
"I didn't say that I can't directly date you," Rob refutes. "Obviously, you know that we have a problem because of a long distance issue, correct?"
Ana says, "How are you supposed to change your act if you were with her Friday night?"
"Yeah, I was," says Rob.
"And you were with me Saturday night," says Ana.
Mai-Lan chimes in, "I'm glad I'm out of the picture. I'm sorry, no offense to you two, but seriously."
"No, none taken," Ana says. "Good for you."
"You really do need a lot of help Rob," Mai-Lan concludes.
Dr. Phil turns to Rob. "What is your position with Ana?" he asks.
"She already knows this. I'm dating her," Rob replies.
"No, I don't think I do," says Ana. "When I talk to you, do you just nod your head? And do you truly listen now? Where do you stand? Like, who are you? Please tell me."
"Where do I stand?" asks Rob. "I mean, yeah, it sucks that I have to date a couple girls just to see if I'm really into them."
"That doesn't work for me, Rob," says a furious Ana. "My time is precious, OK? You could be trophy boy over there but I'm a good-looking girl. I'm not dumb; I'm smart, and I deserve to be treated with respect."
Rob says, "The thing that I could say to all of you guys, I guess, is the fact that I maybe have misled a little bit — not a whole lot — I mean, I truly do care about you guys, so I'm sorry if I misled you, but I want to get to know you guys."
"How could you possibly want to get to know me better if you just said that, 'I'm not that into her, and she forces herself on me'?" asks Ana, incredulously.
"Because you're starting to push me away a little bit," Rob says.
"Consider yourself pushed," she replies.
"Well, I'm sorry if you feel that way," says Rob.
"No you're not," she shoots back.
Rob tells Dr. Phil that he does truly care about these three women.
"So, you cared about Mai-Lan when you were with her; and Veronica, you cared about her Friday night; and Ana, you cared about her Saturday night," says Dr. Phil. Rob says yes.
"To you, it might be, 'I'm just having fun and doing what guys do,' but to them, they value and honor relationships more than that," says Dr. Phil. "And you can say, 'Well, I didn't mislead them. I didn't tell her that.' It's not a matter of whether you tell her that; it's a matter of whether you allow the implication to breathe. You need to be honest with yourself. And you said, 'I recognize —- '" He's cut short by Rob.
"Well, being honest with myself —- " Rob begins.
"Excuse me," says Dr. Phil. "You said you wanted to know what my thinking was. Do you or not?"
"Yes, I do," says Rob. "Proceed."
"I'll proceed when I want to proceed," Dr. Phil says firmly. "I don't need your permission to do it, let me assure you of that."
"I just wanted to know, why am I afraid of commitment?" says Rob.
"I don't think you're at that point yet, and I don't think you understand the gravity that it has on the other side."
Gesturing to each of the women, Dr. Phil says, "This girl's not dumb, this girl's not dumb, this girl's not dumb. Let me tell you, they're not, so you're wrong about that. They're just trusting. Do these look like happy people? This is the aftermath that you leave behind when you do what you do. You don't run from commitment because you've never approached commitment. It's just always been in the moment. Is there anything wrong with that? No, as long as everybody knows the name of the game."
Dr. Phil dismisses Veronica, Mai-Lan and Rob, but Ana stays behind.
Sitting alone together, Dr. Phil asks, "Do you think he gets it?"
"No," says Ana.
"To his credit," says Dr. Phil, "y'all haven't known each other very long. Do I think he's a bad guy? I really don't. I just think his insight into intimacy and commitment is zero. You know it now. He's highly suspect, right?" Ana nods in agreement.
"Your feelings are for who you wish he was instead of who he is. And you don't have to settle for that. Don't. Don't," he impresses upon her.
"I won't," she says. "Otherwise, I really didn't learn my lesson."