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Mastering Your Modern Dating Game (Part 2)
Webinar hosted by Victoria Joseph of ENMMATCHMAKER
Getting matched is one thing. Getting off the apps and into the same room is another. Part two of this webinar series picks up where part one ended, with photos and bios already sorted and conversations running well, so ENM matchmaker and dating strategist Victoria takes it from there and walks through what happens once two people are finally in the same room.
Why Activity Dates Beat Plain Dinners
Victoria's favorite example comes from her own life. She and her husband were each chatting with a different couple on Feeld, and with two conversations at risk of fizzling, she organized a group double-double date: all six of them kayaking on the Chicago River. Two to three years later, everyone's still friends. Her takeaway is that activity dates are strategic. Shared experience gives people something to bond over, keeps hands and nerves busy, softens those first few minutes, and helps first-timers relax far faster than sitting across a table under fluorescent-adjacent pressure. For anyone anxious about that first meeting, an activity does a lot of the emotional heavy lifting.
Logistics That Signal Care
When meeting a single, especially a woman or "unicorn," Victoria recommends offering to sponsor a rideshare. Both Uber and Lyft have a setting that lets someone else cover the fare, which means she doesn't have to be picked up by a stranger or wrestle with parking in an unfamiliar neighborhood. That's a small gesture with a big message: her safety and comfort came first, before anyone even said hello.
Be Early, Not On Time
Victoria's punctuality trick is simple. Aim to arrive 10 to 15 minutes early, and if the reservation's at 7:30 p.m., "lie to yourself and say it's 7:15." Build the buffer into your own head so you're never the one rushing in flustered. Extend grace to your dates if they run behind, but hold yourself to a tighter standard. Being settled and unhurried when they walk in sets the tone for the whole evening.
Dress to Impress
The goal is clothing that's comfortable and well-fitted, so nothing about your outfit distracts you during the date. Comfortable still means put together. Victoria was direct: no hoodies, no ripped jeans, no dirty sneakers, and nothing you'd wear to run errands. Men can lean on a button-up, short or long sleeve depending on the season. Women can lean a little sexy. The same standard applies to clubs and events, not just restaurants, and as Victoria put it, looks matter, especially when it comes to men.
Date Etiquette and the Table Plan
The fundamentals are unglamorous and effective. Maintain eye contact and try to make your date laugh so you become associated with positive feelings, and don't dominate the conversation. If the date ends and you know nothing about them, it probably isn't going anywhere. Victoria also offered a concrete table plan: share an appetizer, keep it to two drinks maximum, enough to settle your nerves without slurring your words or running up the bill, enjoy a meal, and then dessert if the mood is right. And match your date's eating pace. If they're nibbling slowly while you scarf your plate, they'll feel awkward. Take turns carrying the conversation so everyone actually has room to eat, and consider splitting a salad or entrée, since restaurant portions are often enormous anyway.
Order With the Rest of the Night in Mind
If the date might lead to sex, what you order matters. Victoria's advice is to keep the meal light so you're not feeling crampy or bloated later. And her hot tip of the night: beware of cheese. As she explained it, "little things might slip out while you're having sex, and that's all because of what you had for dinner."
Who Pays, and How to Bring Up the Hotel
The general norm Victoria described is that whoever planned the date should offer to pay. If you're taking out a unicorn or single woman, you cover the bill. Couple-to-couple, the default is splitting 50/50 on the meal and 50/50 on the hotel, or negotiating so one couple sponsors dinner while the other covers the room. She also recommends mentioning the hotel early, with explicit no-pressure framing: "Hey, I'm gonna cover the hotel, just so you know, but no expectations." That one line quietly signals that packing a bag might be a good idea, and it leaves consent wide open so nobody feels cornered.
Graceful Exits and the Follow-Up
Plenty of good dates should end at the curb, and Victoria was emphatic about that. If the enthusiasm isn't there, say you don't feel well or you're not in the mood. In her words, "don't take one for the team." Aim to leave with no regrets, and read social cues carefully so a lack of enthusiasm on either side doesn't get taken personally. When the enthusiasm is there, momentum matters. Text the next day, tell them you had a great time and want to see them again, then start planning the next one. That single message turns a good night into a connection that's actually going somewhere.
Mentoring Newcomers and Reading the Room
Victoria enjoys using her local knowledge of clubs to guide new couples, because she genuinely wants people to enter the lifestyle and stay in it. Her encouragement to experienced members is to share your good experiences openly. She also urges sensitivity. If a new couple seems nervous or overwhelmed by direct sex talk, pivot to questions about them, like what they're looking for and why they got started. You'll gauge connection just as accurately, and they'll walk away feeling welcomed instead of hurried.
Clubs, Resorts, and Singles Admission
By reputation, Victoria has heard good things about Temptation and Desire in Mexico, though she hasn't been personally, and she also named Cap d'Agde in France. Her broader philosophy is to explore clubs worldwide while making repeat visits to your favorites, and if your goal is building local friendships, prioritize venues close to home. On whether singles can attend, her answer is that admission varies entirely by club and location. Some allow single men and some don't, and some resorts require even single women to attend with a partner. Always check before you book.
Photos and the Sober Lifestyle
Returning briefly to profiles, Victoria's guidance is quality over quantity, with more photos generally being better. Use good lighting, show your face, and keep things tasteful and teasing. She cautions against bad genital pictures, because a single off-putting photo can undo the impression made by all the others. For those who don't drink or party, she acknowledges that people at events are often "enhanced," and there are still clear ways in. Search website subgroups and group chats labeled "sober play" or "sober swingers," state your sobriety preference directly in your profile, and lean on activity dates when a party doesn't appeal. A nearby outing gives you connection without the bar.
Original webinar was live-streamed on SDC.com on Tuesday, March 17, 2026
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