To say "I love you," or not to say "I love you," that is the question…for Blair (Leighton Meester) at least. Her dry spell from Chuck (Ed Westwick) has her taking matters into her own hands, literally. Chuck won't give Blair the time of day unless she says "I love you." So, Blair has a conundrum; the only thing to do when one has a conundrum brewing is to talk to the best friend. Ever since the treacherous trip to Yale, Serena (Blake Lively) and Blair are back on the right track to being best friends. This does, unfortunately, require Serena to hear about Blair's itches that only Chuck can scratch. Since Dan (Penn Badgley) and Serena also seem to be trying out the friend scenario, this also requires Dan to listen to Blair's problems.

Dan encourages Blair to become unavoidable to Chuck. This, however, fails. Blair tempts Chuck with drinks at a bar and then tries to seduce him with her lovely neckline and by spilling cocktails on his pants. Chuck, on the other hand, simply remarks, "I'm bored, and you've ruined my pants." So he takes off, leaving Blair flabbergasted. Now Dan has Blair calling him, asking him what to do next! Finally Dan just asks why Blair can't say "I love you" to Chuck. She claims she can't let him win this game. And that's the kicker…Blair and Chuck love to play games with each other, and as Dan finds out, with Vanessa (Jessica Szohr). After spilling his heart out to Blair about proclaiming the three word phrase, Dan discovers from Vanessa the little trick the two played on her last week. Dan's loyalties kick into gear and he stops Blair right before she is about to proclaim her love for Chuck; Dan tells her to make sure Chuck is through playing games. This simple statement makes Blair rethink her entire "honesty is best" strategy. Her and Chuck end the night still without any "I love you's" and probably more depressed than when they began their game. Chuck throws out the typical boy answer of, "I'm not sure how long we'd last or if we'd like being a couple….We like this [playing games]." The two have a silent farewell with only a touch of the hand.

Blair isn't the only girl on the Upper East Side with boy problems. With a new found friendship budding between Dan and Serena, it doesn't seem so coincidental that a nice stranger from Serena's past would suddenly emerge. It's always something to keep these two apart. Rufus Humphrey's (Matthew Settle) art gallery is having an opening with an up and coming artist, Aaron Rose (John Patrick Amedori), who just happened to attend summer camp with Serena. They even got married with licorice rings and everything! But, when Serena realizes this, tells Dan of her potential feelings for Aaron and then rushes to meet him, she finds him driving off on his motorcycle with another girl. Poor Serena? Not really, I'm still questioning why she and Dan don't just get back together already…we all know it'll happen eventually.

And then there's Jenny (Taylor Momsen) and her dreams of being a fashion designer. That dream is proving hard considering Eleanor Waldorf (Margaret Colin) is using all of Jenny's designs for her profit…and not even letting Jenny sit in on the meetings with the buyers. However, Jenny meets O.C. alum Willa Holland portraying a model named Agnes out to jumpstart Jenny's career with her boyfriend Max, the photographer. Together the three spend a wild evening out at a trashy bar. The photographs of Agnes in Jenny's clothes "looked like an ad campaign." Agnes convinces Jenny that when she does break out on her own she won't want her designs to resemble Eleanor Waldorf's designs, so she needs to get out now. Jenny decides to do just that, even taking back the dress Serena wore at Eleanor's Fashion Week show. But, Agnes isn't the only one looking out for Jenny. Nate (Chace Crawford) has been paying more attention to Jenny in this episode than he has since last season. It all started with an awkward encounter in the bathroom with a shirtless Nate and a newly blonde Jenny. There was some speculation that Jenny and Nate were sort of into each other last season, back when Jenny and Blair were feuding, but that's long since died down. But, now that Nate is staying at the Humphrey home, I guess all bets are off. Jenny tells Nate she's going to start her own line with the help of Agnes and Max and he is concerned, not excited. He follows her to an apartment where she ends up half-naked with Agnes and Max; no, not in a sexual way, they were just goofing around. Nate is determined to get Jenny out of this bad situation. Jenny then is rescued from this situation (which never actually turned bad) by her "knight in shining Armani." She asks why he cares so much, and then they embrace in a kiss in the middle of the sidewalk. Not like we didn't see this coming from earlier on in the episode, but it is a little odd to throw this romance out there mid-season. Those in charge of the show have been known to bring some ideas truly out of left field; guess they just needed something to spice up November sweeps.

Gossip Girl stars: Blake Lively / Chace Crawford / Leighton Meester / Penn Badgley / Ed Westwick / Taylor Momsen / Jessica Szohr / Kristen Bell / more

Story by Beth Wickman

Starpulse contributing writer