Wait, how do you know he's on these sites? Do you have a profile as well?? Were you surfing for dudes and your guy came up?? That's like the beginning of a Kate Hudson movie. Or the "Pina Colada" song, where the guy takes out an ad in the personal column and then his wife ends up answering it. Can you believe people used date through the newspaper? That's crazy that people used to go on dates based on reading "SWF seeks SWM for long walks on the beach and candlelit dinners." 

I'm kidding, of course. Clearly you were snooping on him. Not a good idea either. Why not ask him why he's keeping the profiles? I agree that it's lame and slightly shady to be "in a relationship" on a dating site. For one thing, I feel bad for single people cruising the site who have to click past this profile. Keeping his profile is like keeping his apartment or having a storage locker for his stuff after you've already moved in together-- it's like an escape route. He's saying, well, if this all falls apart, I still have my online dating profiles. It doesn't necessarily mean he's looking to cheat, but it's not a ringing endorsement of his long-term commitment. 

Let him know how you feel. There's really no good reason for him to keep those profiles if he's really committed. People, get off dating sites if you're in a committed relationship. Don't just change your status. Match.com is not Facebook.

Update! There's a happy ending to this tale! The worried woman in question took the (shocking!) step of actually asking her man about his dating profiles instead of stewing in silence. He sounded legitimately surprised, explained they were old profiles he'd forgotten about and deleted all of them within five minutes of his lady's request. Sounds like a man of action - and a keeper - to me. 

Let's run your question through the Wise-Ass Translator O' Truth (patent pending) and see what we get:

Does that sound about right? Now you know what is happening. Proceed accordingly.

This sounds like an ex-clusive relationship. Get out while you can -- you've got a chorus of commenters urging you to stay strong. p.s. Do they sell the Wise-Ass Translator O'Truth at Target? Because I would buy one in a heartbeat. Until then, thank goodness we have all the Guyspeak guys - and wonderful commenters - translating our heartaches into truth. 

There is something to be said about making sure you've got some solid bread before slathering on the sex-onnaise. This guy might be legit and wanting to make sure your foundation is in place. Is it suspect? That proof will be in his putting in the time and actually developing your relationship. Walks, dinners, phone calls, emails, museum nights and Socratic debate over a shared bowl of calamari. If things like this don't happen, and in its place are tumble weeds and crickets, then he was lying.

Unfortunately, sometimes, man has sex, doesn't like the sex or the person and rather than having the balls to respectfully end it, he creates stories and fictitious plans. I hope that's not the case if you dig this dude. Take it slow, (as he suggests). See if he's peddling towards you or back - and respond accordingly.

Call me a cynic, but I highly doubt this man is being straight with you. If he didn't worry about building a relationship the first time you had sex, it seems odd that he'd be so concerned with that now. Possible, but odd. The thing about guys is, they're terrified you're going to cry. And they're afraid that if they say, "I just wanted sex from you - I got it, I'm good now," you might start crying. So they say something that *sounds* thoughtful and mature to avoid hurting your feelings. But I haven't seen too many men in real life who put the brakes on sex with someone they're digging. As Amit says, watch which way this guy is peddling. It's the direction his feet move, not the direction his mouth mumbles, that'll tell you which way he's really heading.

Girl, you betta work it. Do YO thang. I don't know that there's ever a wrong time. He will love to get those pictures at any time of day. Now, he might need a slight heads up on the ones he receives at work because you don't want him to get a text at a meeting and then open it up to your boobs and somebody's looking over his shoulder. That would just be awkward. 

Early in the morning nudity is always a good thing though. As is the pics a few hours before you see him to let him know what's waiting on him. We love to hurry up and wait.

I just think it's fun that you want to send such pictures and are taking control of your body and image. Your man will love the fun-loving nature of it and will provide you all of the compliments and excitement you need to send more. So send away. Send with reckless abandon.

I think this is a fabulous idea if executed safely! As many of the commenters pointed out, these sexy shots are safer sent without your pretty face in the pic. If heaven forbid you break up with the lucky recipient - or click "boss" on your contact list instead of "boyfriend" - you will be forever glad your face wasn't connected to your naughty bits. As for time of day - you'll get the most bang for your buck (so to speak) if you send it a few hours before you're going to see him. Think of it as an appetizer before the main course. 

If you don't want to be humiliated, simply don't tell him.

Sure, you tell him about the depression as needed, that is a given, as it is something that can seriously affect how the relationship runs. But your sexual experience, or lack of it, is really none of his business!

Why people insist on thinking they have the right to know everything about their partner, and the obligation to spill their guts on first meeting is totally beyond me, and is going to be part of next weeks blog post. So, get your game face on and get out there. Inexperience won't fix itself, you know!

When a toddler takes a tumble, the biggest factor in whether he dissolves into tears or giggles is the nearest adult's panic level. If the kid gets the "oh my God, you could have been killed!" look, cue the waterworks. If the grownups give the "no biggie, little buddy" glance, the kid will move on without much fuss. Same thing applies to relationships. The way you approach a "scary" moment will greatly impact how your partner reacts. Mystery Man might have a point here. If you don't make a big thing about losing your virginity in front of this guy (by not mentioning it at all), he's not going to make a big thing about it either. Or you can be up front in a fun, cheeky way. Say something like, "I haven't had a ton of practice in this subject, so if you have any lessons to teach me, I'd love to stay after class and learn."  

Think for a minute how'd you feel if one of them casually mentioned another woman he was seeing, and when you say "Why didn't you bring this up?", he says, "You didn't ask." You'd think he was a jerk, right?

Come on, this one isn't really that hard. They may not be talking exclusivity or asking about your sex life beyond them, but they definitely might be assuming they're the only person on your dance card. They've got a right to know where they stand.

That said, they also don't have a right to be that upset; they were the one making an assumption, after all. Just be prepared for a little flack, and possibly a dumping.

Sorry, Dan, I have to completely disagree. There's no way this information needs to be volunteered until it's asked for. It would be silly and potentially insulting to brag about how many other people you're both dating before you're ready to have the exclusivity talk. Until then, we all know the rules of the game -- presume multiple partners until told otherwise. 

And with that, the game's over for this week. Thanks for playing, guys and girls!