For daters: Silver Spring’s 8407 Kitchen Bar can be a great place to meet older singles — or simply plan a great date in the suburbs. (Sean McCormick/For The Washington Post)

Our two dating experts, author Jess McCann and Meetup organizer Rita Colbert (who embarked on a project to go on 35 dates in 35 days), took on some tough questions about relationships and dating in D.C. and the ’burbs, while readers submitted their best ideas for holiday dates (one particularly innovative reader netted an $85 gift card to dine at the Palm).

We’ll round up the best holiday date ideas from the chat in a separate post. In the meantime, check out some of the best advice from this epic chat below. And be sure to join us on Dec. 22 when we bring back the lovely Holly Thomas, former Guru and the newly minted editor of Refinery 29’s D.C. edition, for an all-things New Year’s chat, covering where to go and what to wear.

Q: After the fifth date , who contacts whom? Should the girl still wait for the guy to contact her and ask her out?

Jess McCann: Until you are in an exclusive relationship, the guy always contacts you first. It’s the only way to know exactly where you stand with him until you have the talk. Plus, you have to let him pursue you! And sending even a small innocuous text like, “how was your day” tells him you are thinking about him -- and when he’s chasing you, he’s not supposed to know that!

Q. I am a single 40-year-old female who lives in Silver Spring. Where are some good places in that area that I can go to during the holidays (or any time really) to meet single men my age or older (40s/50s)? I would love to find a spot where I could go on weeknights/ weekends to get a bite to eat and maybe chat with some friendly folks. Basically, I am looking for my “Cheers” in Silver Spring. Any advice would be much appreciated. Thanks!

Fritz Hahn: The bar at 8407 would be my first choice -- cool lounge, friendly bartenders, great food and drinks. If you go a little further north, the Limerick Pub in Wheaton gets a crowd that ranges from 20-somethings to families to singles in their 30s, 40s and older.

Lavanya Ramanathan: I’d also recommend a couple of other options that can help make any place your sort of “Cheers.” There’s a popular list serve called PaulsList that you can sign up for by e-mailing It was suggested to me as a popular way to meet people in their 40s and up in Maryland in particular. And several women I’ve interviewed really liked the events they attended through the listserve. And try, too; it’s another clearinghouse for dating events and mixers and happy hours.

Q. What is a nice, relaxed, quaint cozy bar with a fireplace and specialty drinks?

Fritz Hahn: The Tabard Inn is the go-to, and for good reason -- especially if you go on a Wednesday or Thursday, when head mixologist Chantal Tseng is whipping up one-night-only hot cocktails. Room 11 is a favorite, through its fire is outside on the patio, not in a fireplace. And it’s hard to beat the fire at the Ritz-Carlton in Georgetown, especially when the staff is passing out free s’mores.

Wine by the fire at Sonoma is always fun, though there’s the caveat that the upstairs lounge is frequently closed for private events during the holiday season.

Also, while they’re more traditional Irish pubs, meaning Guinness instead of cocktails, I do love the fires at Murphy’s of Alexandria and Nanny O’Brien’s.

Q: What is the most important thing for single ladies to keep in mind during the holiday season, if feeling down about being alone?

Rita Colbert: That being single doesn’t mean being “lonely”! In one of my blog posts about my dates, I realized that for the past 14 years, I’ve been in a serious relationship in some form or another. It was because I had the mentality that being single meant being lonely. Because of this, I was putting that “vibe” out there for all to see. Who would be attracted to a girl who was sad or lonely -- especially when that’s due to the lack of a man in her life? I can tell you who -- no one. So I kept the cycle going of me being the one without the dates while everyone around me had plenty. What I realized is, the girls who attract the dates are the ones who are perfectly happy in their “singleness.” They are busy, active, smiling when they are out and truly having a great time with their friends, on their own and with whatever they do!