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When Anna, 27, started seeing Brian, it was a dating dream come true. “At first, we had so much fun it was like walking on air,” she remembered. But after two blissful months, Brian’s carefree attitude began to morph into melancholy. “I couldn’t figure out why he was acting so distant,” admits Anna. “Then he confessed that he still had feelings for his ex.” Ouch.

There’s a point in every relationship when the warm, fuzzy fog of infatuation lifts and you’re forced to face reality—that you honey may have issues that could hamper happy coupledom. To Anna, Brian’s admission felt like a slap in the face, but she may have been able to brace herself for the blow if she’d taken the time to assess how well he’s weathered romantic ups and downs. “Since previous relationships have fallen short, there are bound to be fears and doubts that need to be worked through,” says Gaile Prince, co-author of Soul Dating to Soul Mating (Perigee, 1999).

To size up his emotional deadweight, check to see if he’s carting a one-, two-, or three-bag load, then follow our expert advice.

Boyfriend Baggage Key
Miniscule *
Minor Problem **
Major Obstacle ***

He’s on the Rebound
Anyone who’s survived a big breakup knows that the recovery period is riddled with loneliness, anger, hurt, and an overwhelming urge to start dating someone—anyone—to get your mind off of your ex. So how do you know if a guy is truly vying for you and not just trying to fill a void? “It depends on whether he’s dealt with his emotions,” says Elizabeth Hurchalla, author of Getting Over Him (Avon, 1997). To find out if he has, ask him about it and monitor how he reacts.

He’s able to talk about it freely. *
When Jenni, 26, met Jack, 28, he had just gotten out of a three-year relationship. “When I heard they’d broken up just a month before, I was like ‘Forget it,’” recalls Jenni. But Jack refused to give up until she agreed to go on a date with him. “He told me that the relationship had been strained for over a year,” continues Jenni. “And he seemed genuinely happy that things had finally been resolved, so I decided to keep seeing him.”

Jenni was right to interpret Jack’s openness about his ex as a good sign. “If he can discuss his former relationship without obsessing over it, he’s probably ready to start over,” confirms Hurchalla.

He’ll talk about it only if you pry. **
If getting your new guy to spill about his prior love is like pulling teeth, things aren’t completely resolved, says Richard H. Pfeiffer, director of Growth Central, a NYC relationship therapy program (growthgroups.com). But don’t panic. “He may just be a little hurt, confused, or disappointed—which is normal.” Empathize with how difficult ending a relationship can be, but communicate that it’s important for you to know that he’s ready to move o n. If he attempts to open up, he’s one step closer to making his ex a permanent part of his past.

He refuses to mention her name—or talks about her incessantly. ***
Both of these bothersome behaviors are major red flags. “If he never, ever utters her name, it could mean he’s emotionally shut down, which doesn’t bode well for you,” explains Prince. On the flip side, “If he talks about her nonstop, there’s definitely a third person loitering in your love life.” Though opposite reactions, they both indicate the same thing. He’s not prime for boyfriend picking.

His Ex Cheated
Few things are more integral to a healthy relationship than trust. And if your guy’s former flame was a two-timer, he may be paranoid that the past will repeat itself. Your task? To figure out whether he considers a woman guilty until proven innocent or if he still has faith in the fairer sex.

He blames her and only her. *
“When Mark told me his last girlfriend slept around on him several times, I was a little worried,” admits 25-year-old Amy. “But he’s shown me though his actions that he has no intention of punishing me for her mistakes.” Says Pfeiffer: “If he gives you the opportunity to prove that you’re not cut from the same cloth as his cheating ex by reserving judgment, it shows that his negative experience hasn’t crushed his ability to trust.”

He’s sometimes suspicious. **
Naturally, being betrayed is going to make a guy eager to watch his own back, so cut him some slack when he asks where you’re headed on girls’ night out. At this point, he may just need reassurance. “By happily answering his questions, you’re letting him know that you have nothing to hide,” says Prince. “It might also help to emphasize how important honesty is to you.” Another tip: Always keep your word, even about little things, in order to help restore his ability to trust.

He monitors every move. ***
When Alicia’s boyfriend, George, 29, bought her a phone so he could “always know where she was,” the 25-year-old knew he was way too controlling. “George’s last girlfriend cheated on him with his best friend, so he wanted to keep me on a short leash. That wasn’t acceptable.” If your new paramour acts like a probation officer, it’s time to fly the coop.

He’s Never Been in a Long-Term Relationship
A guy with a dating track record that’s all sprints and no marathons could be a classic commitment-phobe, but don’t jump to negative conclusions without considering some alternative causes.

He keeps meeting Miss Wrong. *
Twenty-six-year-old Jeannie had her doubts when she met Henry who, at 31, had never been in a relationship that lasted longer than six months. “I figured there was probably something wrong with him—not them, but I decided to find out for myself,” Jeannie remembers. That was five years ago and they’re still going strong. “When a man repeatedly chooses bad relationship candidates, it may be that subconsciously he isn’t ready to share his life or honestly just hasn’t met the right person,” says Hurchalla. So try a little patience. You’ll find out soon enough if you’re the person he wants to break his breakup high score with.

He’s playing it safe. **
In the not-so-distant past, your man may have had his heart trampled by a woman he hoped might be The One. The result? He’s been nipping relationships in the bud ever since to avoid being burned again. “A guy who’s experienced a painful rejection is bound to be wary of putting his feelings on the line,” confirms Pfeiffer. “Try to make him more secure by verbalizing your feelings for him. The more confident he is about where he stands in your eyes, the braver he’ll be about trying once again to go the distance.

He keeps getting dumped. ***
Even though Melanie had heard that none of John’s girlfriends stuck around for long, she was willing to keep an open mind. “He seemed like a nice guy,” says Melanie, 27. But soon his true colors surfaced. “He never said anything blatantly misogynistic, but he’d make remarks that could be construed as derogatory toward women,” remembers Melanie. As more time went by, John’s anti-woman attitude began to influence how he treated Melanie—with less and less respect. That’s when she decided to dig a little deeper and uncovered that John like a nice guy,” says Melanie, 27. But soon his true colors surfaced. “He never said anything blatantly misogynistic, but he’d make remarks that could be construed as derogatory toward women,” remembers Melanie.

As more time went by, John’s anti-woman attitude began to influence how he treated Melanie—with less and less respect. That’s when she decided to dig a little deeper and uncovered that John had been kicked to the curb by a chick he was really into. “He was seeking revenge on all womankind—one girlfriend at a time—and I wasn’t about to be his verbal punching bag,” says Melanie. No matter how tempting it is, trying to turn a jack-ass into a gentleman is usually an exercise in futility. “If someone has a history of treating people poorly, he probably has very low self-worth,” warns Prince. “So your best bet is to forgo getting involved and suggest he seek counseling.”

Get Your Guy to Open Up
Here, tips on how to suss out his emotional status…sensitively.

Talk in a safe place. If you want him to feel totally at ease, hold your discussion on neutral territory.

Do it sober. A few margaritas might provide him some liquid courage, but drinking causes you to overreact. Another point: If he bares his soul, you’ll want to remember what he said.

Watch your language. If you’re having a heart-to-heart because something’s on your mind, choose your words carefully. Use “I” language. Say “I feel this way when such and such happens.” That way he won’t feel like he’s under attack.