Expert Tips for Having Fun on a First Date — Featuring Matchmakers in the City

Dating is supposed to be fun. It is supposed to bring romance and excitement to everyday life. But those of us who have been in the trenches of online dating or gone through a carousel of bad first dates know perfectly well that it isn’t always fun. Sometimes it’s a chore, and sometimes it’s nerve-wracking, and sometimes it is the last thing you want to do in your free time.

Despite the challenges, it’s important to find the fun wherever and whenever you can in the dating world. After all, the attitude you bring to it can make a big difference in the end result. 

As single people come out of the COVID-19 pandemic with a new perspective, we thought it’d be a good idea to highlight ways to enhance the first date experience. And, yes, try to have fun with it.

Alessandra Conti, Celebrity Matchmaker at Matchmakers In The City, has been a close confidant and guide for countless singles in the U.S., and she has many practical insights on how to approach a first date with confidence, joy, and hope. Over the last decade, Alessandra has helped her matchmaking clients overcome internal blocks and external obstacles on their way to love. 

Matchmakers in the City has its headquarters in Los Angeles — a city bursting with single professionals who have big dreams and high expectations. Alessandra has been featured as the go-to Celebrity Matchmaker for NBC’s “Access Hollywood,” and she created the expert matches for two seasons to MTV’s hit reality show “Are You the One?”

When she’s not matchmaking celebs, Alessandra works with many down-to-earth single professionals who are over the online dating scene and want to find a serious partner. She works alongside the team of Matchmakers at MITC. “It’s such a rewarding career to see so many marriages — and babies too!” she said.

A major part of Alessandra’s job is date coaching singles who haven’t quite mastered the art of attraction or the conversational tools needed to find common ground. She also works on reframing her client’s expectations by making sure their dealmakers or dealbreakers are justified and consistent with their own lifestyle.

She urges singles to avoid snap judgments on a first date and give people time to reveal their true nature and positive qualities.

“I have worked with people who say that they know immediately when they don’t like someone. This is setting yourself up for ultimate failure,” Alessandra said. “While love at first sight is amazing in romantic comedies, a majority of the time in real life, love takes time to grow.  Lust at first sight is great, but it in no way will determine the quality of a long-term relationship.”

Thanks to her unique perspective, Alessandra can share a lot of insights into what singles can do to change their mindset and enjoy their first dates.

“A lot of times, singles go into first dates as if they were a job interview.  They take them incredibly seriously,” Alessandra told us. “While dating with intention is important, there is a fine line. Dating needs to be fun — if you’re not enjoying yourself, you better believe the person on the date with you isn’t either!”

So, what can singles do to end the interview and enjoy dating? Alessandra said it’s important to approach preparing for a date with an upbeat “vacation mindset.” Maybe that means turning off work notifications or picking out a colorful outfit. Give yourself plenty of time to get ready and feel confident in how you look and what you have to offer your date.

Alessandra recommends setting aside about an hour before the first date to relax and pump yourself up. Play some fun pre-date music, dance a little to loosen up, and use positive affirmations to get in the right mindset.

First dates that involve activities can be great icebreakers because you can talk about your shared experience and don’t have to keep coming up with get-to-know-you questions. However, some singles don’t want the activity — whether it’s pottery, ice skating, or putt-putt golf — to distract from actually getting to know someone, and that’s why dinner dates and coffee dates continue to be fairly common, even during the pandemic.

Alessandra said she enjoys giving her clients the VIP experience by booking a reservation at a romantic restaurant or rooftop bar in Beverly Hills. The team makes the arrangements, so all the couple has to do is show up and engage in a good conversation.

“Great conversation starters begin with topics that you actually enjoy talking about,” Alessandra told us. “If you have fond memories of the 1990s, talk about your favorite Spice Girl, or ask your date who their favorite Disney Princess is. If you love sports, ask them if they play any sports for fun, or if they played any sports when they were younger.”

Alessandra recommends that singles talk about the things that interest them — sports, music, movies, or hobbies — as well as the things they have experienced in their lives. A date conversation doesn’t have to stay on the surface level either. Singles can ask icebreaker questions about a childhood hero or a mentor from school and how those role models shaped who they are today. 

“Connecting on nostalgia is a wonderful way of breaking down each other’s figurative masks that singles inevitably wear on a first date,” Alessandra explained.

It’s also a good idea to talk about plans for the future so the other person can see whether your goals fit with theirs. Singles can have fun talking about the places they want to go or the life they hope to build, and that can strengthen their blossoming relationship.

Of course, not all topics of conversation are appropriate for first dates. Alessandra has seen many clients slip up by getting into some no-go areas. For instance, talking politics on a first date is widely frowned upon, and it can be a quick way to turn a person off or change the vibe of the date to more of a debate than a fun outing.

Alessandra recommends avoiding discussions about negative things — even dwelling on the impact of COVID-19 can be a serious misstep — and trying to keep the tone positive for that initial meeting. 

As the saying goes, people don’t remember what you say; they remember how you make them feel. 

Dating habits have changed a lot over the last year and a half, and Alessandra has seen that firsthand. She told us that she saw many singles buying into hookup culture before social distancing and lockdowns changed their perspective.

“Pre-COVID, hookup culture was at an all-time high. Now people are craving an authentic connection,” Alessandra said. “COVID grounded everyone; for so many busy professionals, it finally gave them a breather to stop and readjust their priorities.”

Many singles have made positive changes in their lives in 2021. They’re hiring matchmakers, they’re joining gyms, and they’re taking steps toward the future they envision for themselves. 

Alessandra said she’s seeing her clients are more open to serious dating experiences and building a relationship that is about more than physical intimacy and chemistry.

“Singles are erring on the side of caution when it comes to hookups,” Alessandra explained. “Authenticity is at the forefront of what people are looking for, and we have very much seen that shift.”

Alessandra said she used to be fervently against kissing on a first date, but she has since changed her mind. During her work as a matchmaker, she has seen many success stories from couples who kissed on the first date. Sometimes the chemistry is right, and both people are open to going for it.

Singles should take their cues from their date when it comes to a kiss or a hug or a simple handshake at the end of the night. If it feels natural at the end of the night, then a quick kiss could be a lovely way to show interest. If the other person is leaning away or trying to leave, then don’t force it. Even if couples don’t come away with a first kiss, their first date could still be a success and warrant a second date.

“As a general rule of thumb, I give a bit of controversial dating advice when it comes to first dates,” Alessandra said. “If you aren’t repulsed by the person, ALWAYS give them a second date (unless they have any big dealbreakers).”

Alessandra told us it’s worth exploring a new connection with someone who shares similar views and has compatible goals in terms of marriage, family, and religion. If those important things are in alignment, then a first impression shouldn’t be the deciding factor to say no. Some people are better at second dates or in relationships, and they have a lot to offer if given the chance.

So how do you express interest after a first date? Text! The man can ask the woman to text him that she got home safely. The woman can then text him to let him know she had a great time, and to thank him for the evening. Traditionally, it is then the man’s job to ask her out again for a second date either via text the next day or even by giving her a call. 

Don’t wait too long (more than a day or two) to follow up after a first date. Today’s singles have plenty of swiping options, and they could move on to someone else if it seems like you’re ghosting them.

Alessandra Conti has been a Celebrity Matchmaker for nearly a decade, and she has seen many love stories blossom. She said the most uplifting part of her job is watching single people open themselves up to the possibility of love with every first date.

We asked Alessandra what advice she has for today’s singles as they navigate the unique challenges of a post-COVID dating scene, and she made it clear that every first date is an opportunity that shouldn’t be taken for granted.

She said sometimes appearances can be deceiving, and a bad first date could lead to a wonderful relationship if singles only have the heart to give someone another chance.

“A first date isn’t a great indicator if a person will be your person,” she said. “In fact, people who are great at dating tend to be not so great at relationships. Sustaining a relationship takes a totally different set of qualities than it does to give off a good first impression. It’s all about consistency!”