The first guy invited me to an afternoon baseball game with a mutual friend. When the friend said he was bringing his new girlfriend, I started to wonder whether this was a double date. We'd never hung out before, so we engaged in typical getting-to-know-you chatter: college, parents, apartments, career plans. I had fun, and by the end of the day was more than a little smitten, talking him up to my friends and hoping we'd get together again, but uncertain as to his interest.

The other guy is a new friend I've had some long, intense phone conversations with, the first featuring three hours of soul-searching as he picked my brain so thoroughly I felt like I'd been to a shrink. He's one of the smartest people I've ever met and he's incredibly charming. When he asked to meet up and talk shop, I agreed, but instead found myself spending a mellow night in a Williamsburg café as the staff hosted an impromptu jam session of ancient Ladino songs with instruments like the oud while pot smoke swirled around us. We sat very close and the mood was intimate, but that was it; he walked me home and I haven't heard from him since.

For my e-mail buddy Dashiell, every date is like this, which isn't puzzling because he deliberately invites confusion into his romantic life. Instead of officially asking a girl out, he'll say, "I've got tickets to this great Ted Leo show, want to go?" I can't blame him, because I've done the exact same thing. Recently, I wanted to ask someone out but wasn't sure how to, so I asked him to a concert. He seemed enthusiastic but had to check his schedule, and when he said he was busy, I let it drop and didn't ask him out again.

At least I'm not the only one who's uncertain about modern dating definitions. Does a date involve kissing? Making future plans? The asker paying for everything? Warm fuzzy feelings? It's hard to tell. Sloane Crosley gives me the funniest answer: "If there's another feasible agenda—professional or a friend of a friend in town—I tend to focus on that and usually don't know it's a date. Not until someone tries to kiss me, and even then I usually file it as an accident of the mouth."

Hailey invokes a word I hear many times in asking about the maybe date: Friendster. A guy wrote to her and seemed decent enough; they went out and she wasn't feeling the vibe, but he was persistent. When he let her use his parking spot while he was away, she wanted to thank him. So as to discourage any potential passes, she chose lunch at Chuck E. Cheese. "Nothing says 'I want to be friends' like a pre-set time limit in the middle of the day at a kids' joint," she writes. Except the clueless guy tried to kiss her in the parking lot, and she finally had to lay her disinterest on the table.

I turn to my musical dating gurus the Hazzards (ukesofhazzard.com), an adorable ukulele duo who opine about just such a situation in their brilliant song "Shut Up and Make Out," for some answers. Anne Harris e-mails: "Clues that you're out on a date that you didn't know was a date are: way too much interest, extra chivalry, a dreamy gaze or two, flirty double entendres, and picking up the check." Later, when I run into her on the street, she says, "Booze is the answer." If only it were as simple as buying someone a beer, I'd be all set.

My wise friend Shari, who's been through her share of dating disasters, thinks the fault lies with unclear planning. "The rules of old-school courting are useful because then everyone knows what the deal is. If someone says, 'I want to take you out to dinner,' I know that it's a date. And if I can't see myself kissing him at the end of the night, I'm not going to accept. I've been on plenty of dates I didn't realize were dates because the guy said, 'Let's hang out' or 'Want to grab a drink?' or 'Let's talk about that idea you had.' "

Greeting-card website Cyranet (cyranet.com) pokes fun at this situation with e-missives bearing lines such as "Are we dating or still just engaging in mutual cooperative stalking?" and "I've enjoyed spending time with you but just can't tell if we're dating. Can I have a hint?" I can't bring myself to send these to either guy (though this column should suffice in that department); I'm too afraid of rejection, so I take the easier route of silence.

Luckily, there's still hope. My friend Nate tells me about a guy who kept going out with his female co-worker. To him, these were simple, platonic outings, but by the sixth one, she was pissed. They had it out, getting into a public fight, which somehow morphed into a hot hookup session, and now they're married!

Lynn Harris, co-creator of breakupgirl.net, finds value in what she calls "vague dates." "Allowing for a little more mystery wouldn't kill any of us. Too many daters date on a need-to-know basis. People are so compelled to define 'where we stand' or 'what this thing is'—two phrases that can suck the life, if not the lust, out of any interaction. So relax. Pay attention to the guy or girl and the date instead of wondering what to call it."

I'm fine with just being friends; it's the ambiguity that drives me mad. The most frustrating part is how quickly I become enamored. I'll admit to dirty daydreams about throwing down with each of them. I want to know what makes these smart, cute guys tick; going only halfway is such a tease. I try to contain myself, but it becomes a balancing act between admitting my infatuation and possibly earning a second, real date and protecting myself emotionally. I'm curious but cautious. Will that stop me from saying yes the next time a cutie says, "Let's hang out"? No, but I'd rather his intentions be clear so I can spend less time questioning and more time, as the Hazzards would say, making out. I do have a sex column to write.

Please visit rachelkramerbussel.com.