Category: First Date Advice

Boston couple walks the dog after a nice lunch date at a romantic restaurant

8 Tips to Rock Your First Date

Is anything more nerve-wracking than going on a first date, particularly a first date after years of being in a relationship or simply not dating? We know it’s not exactly a walk in the park, no matter how many dates you’ve been on throughout your life. Luckily, the expert matchmakers at LunchDates have put together some tips for success on your first date.

Set Expectations

What are you hoping to get out of a first date? Are you looking for some good casual conversation or an instant deep connection with someone? If you’re going on your first date in a while, don’t stress yourself out with the expectation of meeting your soulmate on your first try. It may take a few dates and some trial-and-error before you begin to recognize potential partners that you could “click” with.

Don’t Hesitate to Make the Plans

As a career-minded professional, you’re a busy person. You don’t have the time to spare to go back and forth planning a date. If the other person suggests a date, but doesn’t propose a solid plan, it’s on you to take charge and suggest a time and place.

Choose a Location Within Your Comfort Zone

The more comfortable you feel in your environment, the more confident you’ll be chatting with your date. Pick a place to meet someone that you’ve been to before or one you’re sure you’ll like. Grabbing coffee is a casual, low-commitment way to meet a potential partner; coffee shops are safe public spaces, and if you feel uncomfortable or it isn’t going well, it’s easy to end the date.

Dress to Feel Great About Yourself

Coco Chanel once said, “You can be gorgeous at thirty, charming at forty, and irresistible for the rest of your life.” It doesn’t matter how old you are; if you feel good about yourself and how you look, you’ll be irresistible. Choose an outfit that makes you feel attractive and is appropriate for the setting of your date. Don’t take any chances here, because it’ll show if you’re not feeling great about your outfit.

Be Authentic

You’ve done the hard part; finding a potential partner, setting up a date and choosing the right outfit. Now, you just have to be yourself. Too often men and women both try to be the person they think you want them to be on a first date. Of course, you want to present yourself in the best possible way, but go on the date with no pretensions or affectations.

Have Some Conversation Topics Ready

If you’re not a natural at small talk, conversation can grind to a halt quickly, especially on a date with someone you don’t know very well. Have a few general topics and simple questions in mind. From travel experiences to hobbies, you’re bound to hit on something that will get the conversation flowing.

Don’t Turn Your Date into an Interview

It’s easy to fall into a routine of getting to know someone, particularly if you go on a lot of first dates. While you’re planning out your conversation topics–and while you’re on your date–make sure that your questions aren’t too fact-based. “Where are you from?” and “What do you do for work?” can get old quickly, so be sure to transition those questions into further conversation about your date’s interests.

Let LunchDates Set You Up for Success

LunchDates matchmaking services are a wonderful way to set up a first date. Whether you’re trying to get back into dating after ending a committed relationship, or you simply don’t have the time to seek out someone on your own, our expert dating coaches can set up a casual date with your ideal match. All you have to do is let your personality shine!

Finding Love with LunchDates

The best matchmakers in Boston are ready to help you find love. Over the past 30 years, LunchDates has become known as the most trusted matchmaking service in the greater Boston area. We take the time to get to know you; your likes, dislikes, and all the qualities you’re searching for in a partner. Our professional matchmakers will then match you up with someone who fits those parameters. We can even provide post-date advice! Contact us today to find out more about our services.

Dating in Boston Blog: Guide to surviving a bad date

How to Escape a Bad First Date

Whether you’ve met someone online, through friends, or on your own, nothing prepares you for a bad first date. Bad dating behavior does not discriminate, and affects all ages from 25 to 65. It doesn’t matter if you’re newly single, been dating for a while, or divorced for years. The last thing anyone wants to experience is disappointment. Disappointment over and over again will lead to dating fatigue. Going through the preparation of getting ready, picking out a great outfit, and driving to a destination takes time, energy, and money. So here are some tips I give my clients on how to avoid the minefield of a bad first date:

Bad Date Scenario #1: They don’t look like their pictures.

Remedy: Stop meeting people online. Sorry, but it comes with the territory. 50% of online profiles are falsified in some way. You could ask for a more recent picture before meeting, but there’s really no way to know. It is what it is.

Bad Date Scenario #2: Ex-talk/dating talk.

Remedy: If you find yourself doing this, STOP! If the other person is starting to tread there, politely interrupt and say: “I’ve learned a long time ago to never to talk about ex’s or dating in general. Obviously it didn’t work out for a reason We should always be moving forward and not backwards. Tell me more about…”(Or ask them a question that changes the subject).

Bad Date Scenario #3: They insist on showing you something on their phone. This includes FB pics, dog/animal pics, kid pics, ex pics. (I was once shown someone’s warehouse inventory his company stocked for over 30 minutes!!)

Remedy: Again, be polite and redirect. Say “Hey I’m sure those pictures are great, but I’d really like to learn more about you.” Just try to bridge the conversation. If you have enough rapport with them, you can even put your hand over theirs, slide the phone away as you look into their eyes and say that in a flirty way.

Bad Date Scenario #4: There’s NO CHEMISTRY!

Remedy: First off, are you being too hasty? If you’ve been online dating for a while, the slightest tick could throw you into a tizzy. Assess your state first and foremost, are you being too judgmental? Are you open, happy, positive about meeting this person? You can sabotage potential chemistry if you’re not in the right mindset. If you’re on the fence, give it a little time and definitely a second date, this is an absolute must if you’re not sure.

Bad Date Scenario #5: They keep checking their phone or take a phone call.

Remedy: Admittedly this becomes more difficult when you have kids, but you’re there to meet the other person, not talk on your phone. If you’ve put the time and energy into arranging this date, try to stay polite and positive. Be direct; say something like, “Hey if you’re not enjoying yourself, its ok. We can split the tab and leave.”

Bad Date Scenario #6: The conversation is dragging, too charged (insert political views here), or lacking chemistry.

Remedy: Are you the problem or the solution? If you’re over talking, that’s the number one reason the conversation is lagging. However, if you find yourself clamming up, have a few stories ready. Ideally tell a story that tells them something light-hearted and funny. If the other person is struggling, ask them open ended questions like “So what were you like as a kid?” If you’ve paid attention and picked up on a trait, (like they love to travel) you could also add in “I bet you were always exploring. Maybe even got into trouble once in a while?”

There is no fool proof way to know if a first date will be a hit or a miss. Sometimes things can be going exceptionally well, and then POOF! The other person puts their foot in their mouth. So practice a little compassion and understanding when dealing with another human being. If you are interested enough in the other person, try to do less judging when they’ve messed up, and help them out. At the end of the day, relationships are all about supporting each other. If you can start practicing that on the first date, you’re sure to end up with the right person.

Aimee Burke is a Boston dating coach and matchmaker at LunchDates. Aimee specializes in date coaching for singles in the Boston area. She also serves as an executive matchmaker and recruits professional singles for her clients.

Two singles enjoy Speed dating Boston

10 Steps to Going on a First Date and Loving It

Whether this is your very first or your hundredth first date, everyone gets a little nervous. After all, this could be the one! You could be meeting your soul mate over your first burger together or your first cup of coffee. You might just be meeting someone who could be a great friend for the long haul. Either way, first dates can be intimidating and are full of uncertainty. What is certain, though, is that if you follow these steps, you’ll be on your way to an incredible first date; fun, relaxed and unforgettable.

LunchDates knows first dates. With as much experience as we’ve had pairing up professionals over the past 30 years, we know how many butterflies are in your belly right before your first meeting. Don’t sweat it, though. LunchDates offers the premier dating service for love-seeking professionals in the greater Boston area, and with our one-on-one dating professionals, you know your relationship status is getting undivided attention and care.

1. Relax

This action can seem like an obvious tip, but it’s often the most difficult to achieve or the most likely to be forgotten. You have a lot of thoughts rumbling around your head right now, and relaxation can easily be slid to the back burner.

Clear your head. Before pressing the doorbell, opening the door or picking up the phone, clear your head. Rinse your mind of all the things jumping around in there because everything you’ve been preparing for is happening in real time. When you first say, “Hello,” there’s no more time to prepare, but there is time to take a deep breath, try to calm your nerves and jump right into a memorable first date.

2. Be Yourself

Being your true self is always the safest bet. It sounds cliché and like this could turn into some sort of inspirational monologue, but this is an honest and sincere piece of advice.

Acting like someone you aren’t isn’t only going to be evident to your date, but it’s going to be a hard act to keep up. Your date will be confused the next time you meet and you’re a different version of yourself than you were during your first encounter. If you want things to turn out in the long run, be yourself from the very start. If someone falls for you, you want to be sure they’re falling for the real version of yourself and not the persona you’ve been trying to act like.

3. Premeditate Topics of Conversation

A lot of things can go awry during a first date. Someone is late. The food is awful. Traffic is horrible. You spill on your fancy new duds. Possibilities for minor disasters are virtually endless. Something that could send you into an anxiety-riddled panic, though, is a lull in conversation.

According to this study from the Journal of Experimental Social Psychology, it only takes four seconds for a bout of silence during a conversation to turn awkward. If you want to resist any chance of an awkward moment inviting itself along during your first date, it could be a good idea to keep some topics of conversation tucked away.
Did something funny happen to you that week? Strange? Unusual? Take a mental note—it could be fun to mention and laugh about during your date when you feel a silence encroaching. Don’t divulge too much personal information, though. If you introduce your baggage within hours of meeting each other, things could turn awkward or too serious for a first date.

4. Dress Comfortably

How to dress for your first date is a tricky tango between sweatpants and tuxedos. Despite whether your date is taking place at your favorite park bench or the trendiest steak joint in the city, try to find a happy medium between too casual and too dressy. Maybe nix the black tie attire or ripped-up denim and opt for something a little dressy, but that doesn’t make it seem like you’re trying to out-dress your date.

Just as tip #2 works for personalities, it also applies to your first-date outfit: Be yourself. Don’t dress like someone you aren’t. If you prefer pants to skirts, wear pants! Not into accessorizing? No big deal. Don’t try to look like you were torn right out of a J. Crew magazine if that simply isn’t you. If it is you, then rock that look unapologetically.

5. Clean Up

Good hygiene goes beyond clean teeth and combed hair—it means you have your act together. Cleaning yourself up has a slew of peripheral connotations: you are considerate, responsible, not a child, etc. To someone you’re going on a first date with, these are all good characteristics to accentuate. In a nutshell, being clean and smelling good screams responsibility. Meeting a date after golfing a few rounds or going to your favorite yoga class is only acceptable if you have time to clan up afterwards. Although most adults regularly practice good hygiene, this reminder doesn’t hurt.

6. Ask Questions and Listen Carefully

A first date is a two-way street. If you only wanted to listen to or talk about yourself, you can do that on your own. Going on a first date is a teeter-totter between telling your date all about yourself and listening closely to all they have to say about themselves; be interesting and interested.

In short, don’t be a conversational narcissist. Every conversation is full of initiatives. You can either perform an attention-seeking or an attention-giving initiative. Too many attention-seeking acts and you might just be tipping too far into “me me me” territory. Talking about yourself too much or not engaging in conversation with what your date has to say could leave them feeling restless or dissatisfied with what they wanted to share of themselves. Making others feel unimportant is never a good foot to start on.

Monopolizing conversations from the get-go could make your date feel uninteresting and even have them questioning why they are out with you in the first place. If they can’t get a word in without the conversation turning back to you, chances are good their taste of the first date is a sour one and a second one might be erased from their calendars.

7. Don’t Overdo It

No matter if you go to a baseball game or a trendy bar, don’t overdo it. You may feel nervous for this date, which could cause you to hide your feelings with too much of a good thing, so lowering your inhibitions by guzzling martini after martini isn’t the best idea.

Having a drink or two may be the planned date for the night, but becoming sloppily drunk might send a signal to your date that you’re very uncomfortable in your situation. It could also signify a couple other more negative characteristics such as a lack of self-control, overly impulsive behavior or poor judgment. Whether it’s the number of beers you order or the amount of cologne you put on, it’s safe to err on the side of “less is more.”

8. Use Your Manners

You don’t need to go to etiquette school for this tip. Having manners doesn’t have to correlate with stagnant, stuffy or cold gestures, but instead they can be simple actions. Being courteous to your waiter. Speaking with your inside voice. Not picking food off your date’s plate (unless asked of course). There are a variety of simple ways to exude good manners while impressing your date.

Especially in this age of ubiquitous technology, using good manners reaches into the realm of not checking your phone while on the date or ignoring conversation to check what the score is to a game on a nearby TV. Being present and acting on all of the above tips can help exemplify good manners in their finest forms.

9. Be Good

This is a vague and vast tip. Being good has a cornucopia of iterations, but the goodness I’m talking about is simply being a good person. It’s easier to describe the things that aren’t good and avoid doing them: greed, narcissism, sexism, racism, anger, etc. Being mean and spiteful toward a waiter having a rough night isn’t going to show your date that you’re a very good person.

Being good could range from giving a good tip to the waiter who deserves it, offering to buy dinner or giving a compliment or two to your date. There’s no need to overdo it (see tip #7), but sprinkling in a couple of signs that show your core goodness as a person will never hurt you, especially in a first-date situation.

10. Ask for a Second Date

Lastly, ask for a second date. Maybe your jitters got the better of you. Maybe you had an especially stressful day at work. Maybe you just didn’t feel like yourself. Or maybe this first date was everything you had hoped for and more. Whether you want a redo or some more of the best time ever, ask for a second date. You’ll be able to tell a lot from a second date; whether the sparks are igniting or getting snuffed out will let you know if this is a budding romance, future friendship or total flop. Plus, everyone deserves a second chance.

Dating in Boston Blog: Tips for avoiding a horrific first date

10 Tips On How To Avoid A Horrific First Date

Tis’ the season of thrills and scares. Where everywhere you look your unending thirst for human blood can not be satisfied with even the purest of virgins. Ghouls and goblins run the streets at night as you creep along under the full moon in your short skirt and high heels. I am of course, talking about the dating scene. So in the spirit of all things Halloween-ish, here are my Top 10 Tips on how to avoid a very horrific first date….

Let’s break it down real simple. No tricks, hopefully a few treats!

1. There’s an unusual amount of bad grammar in his profile or he capitalizes in his sentences at odd times. This is equated with a low I.Q. or him not really taking it serious. Next…

2. Pictures are all with sun glasses and/or he’s not smiling. He will have weird eyes and bad teeth. Pics should showcase both so you can check out the goods.

3. You’ve scheduled the first phone call. Yes this is a MUST!! Listen for – weird foreign accent, unusual amount of curse words, and a high pitched voice. Those are all deal breakers (at least they are for me). If there’s an awkward silence or two or he talks without taking a breath, well that’s harder to decipher. Always go with your gut on those talks.

4. He recommends you pick the place, time, and what you’ll be doing. Umm…. no. WTF? Where do these guys come from?

5. He texts you endlessly until the day of the date. Desperate a little? Let us at least think you have a life and are talking to other girls.

6. However, he goes completely dark until the day of the date. This is also bad. Did he just schedule you in because he has an open slot? Bad as well.

7. You’re driving to his town. No. There’s nothing wrong with providing a little guidance when he’s making a decision like, “Hey this street has a lot of good restaurants on it.” OR “Boston’s half way for me. I just need a place with good parking.” There’s also this thing called the internet.

8. He’s late (over 15 minutes). And he doesn’t have a GPS (I know…what??). And he calls you for directions to walk him through getting there. This happened to me about a month ago. It was like talking to my long lost, high-pitched voice cousin from out of town over the phone. It went dramatically down hill from there. Define your own window of allowable lateness.

9. His conversation is too sexual too soon. Ladies you should know this by now. He’s out for one thing. Next!!

10. You pick up the bill completely or split the check. I can’t tell you how many were so close to a second date (still just hoping there’d be a click eventually) until he did that. No way. Never. It’s worth the $30-$40 to show you he’s the man. Relationships are different. But first dates – I guess call me old fashion.

Good luck out there and watch out for poisoned apples! Happy Halloween!!

couple with dating coach enjoys scenic ride downtown

Men’s Guide to Preparing for a First Date

You finally did it. You called the Greater Boston area’s premier matchmaking service LunchDates. Their professional matchmakers took the time to get to know you and they helped to introduce you to your perfect match. Now the time has come and you’re getting ready for your first date.

In your professional life, you don’t leave anything to chance and neither does your date. First impressions are everything. You’ve only got one chance to make a first impression, so make it count. Preparation is the name of the game when it comes to first dates, so here are five key steps for getting ready:

1) Leave your baggage at the door

You’ve got a great date lined up, so relax and have a good time. Whether it’s issues at work or on the home front, you must leave it all behind. Venting about your demanding boss or an ex is a sure fire way to turn people off. Focus on positive things and let the conversation flow.

2) Grooming

Some men just don’t understand that it takes time to look good. Grooming is important. Take the time to get a haircut. If you have a beard, don’t go all Zach Galifianakis and let it grow in a thousand directions. Your date should be impressed by how the beard accents your facial features and not that it hides small animals.

Good grooming also requires that you spend some time on your nails. It should go without saying, but make sure your fingernails are clean and well trimmed. The same holds true for your toenails. Your date may not see them, but you should always be prepared.

3) The Right Clothes Make All the Difference

Dress for the date you want; not the one who’ll settle for you. Like Mark Twain said, “Clothes make the man.” The right clothes can definitely make you more desirable. Dress properly for the occasion. Keep in mind that LunchDates is a premier service and the professional matchmakers will place you with other single like-minded professionals. They use professional and proven matchmaking techniques to pair professionals for dates. That means you can expect your date to be well-dressed and professional. You need to be the same.

The key here is to dress nice without going overboard. You don’t have to wear a tuxedo, but you also don’t want to wear something just because it’s comfortable. And yes, that means your favorite Red Sox T-shirt is out of the question – unless you happen to be going to Fenway. As a general rule, dress slightly better than you think you need to and you’ll be in the right zone of casual vs. dressy.

4) Rules of Engagement

One of the biggest mistakes men make is talking about themselves and not be inquisitive about the person they are with. Of course, the person you’re out with wants to know about you, but it works both ways. Ask questions. Be engaged. This is a date and not an interview, so ask questions to better get to know them. Remember there is no reason to talk about past relationship or previous dating exploits.

5) Smile

It’s been said that the world always looks brighter from behind a smile, so what are you waiting for? Smiling is infectious and can change the whole mood of your date. Remember you want to put your best foot forward so don’t be too guarded or standoffish. Relax, smile and enjoy yourself!

man goes on bad second date

5 Things To Never Tell a Woman on a First Date

With a million ways for a first date to go wrong (and right), take our advice on 5 things you shouldn’t tell a woman on a first date. Even though these may seem very easy to follow, there’s a reason we mention them – people still say them.

Don’t Treat Her Like an Object

When it comes to women, one of the most common fears about the first date is that men will objectify them for their physical beauty, not paying attention on what they have to say. So, saying ‘Can I take your picture?’ or ‘Nice curves!’ will probably get you nowhere. If you add staring inappropriately to this situation, you have a good chance of your first date being your last date.

Avoid Comparing Her to Your Mother

The best way to impress a woman is to treat her like she is one of a kind and avoid any comparisons, especially comparing her to your mother. Mentioning your mother on the first date will make your date think that you are a momma’s boy unable to make decisions on his own. Furthermore, comparing your date to your mother can imply that you are an insecure person looking for the woman to basically replace your mom. Therefore, it is best to leave any mother-related topics alone.

Stop Trying To Save Money on the First Date

A first date isn’t the best time to use a coupon or a Groupon. Being “cheap” or stingy can be a great quality in many life situations, but in the case of the first date it is unacceptable. Making odd faces every time you pull out your wallet and wondering when everything got so expensive will make you look petty. Your date will probably think that you aren’t financially stable, and women look for men that are able to support them through life, not to be supported.

Don’t You Dare Say ‘I Love You’

Expressing your deeper feelings on the first date is strictly forbidden, unless you want to scare your date away. Saying ‘I love you’ to a person you have just met will mean that you are an emotional individual that makes decisions hastily. Besides this, you may not be taken seriously as the words ‘I love you’ should always be said meaningfully. Leave your declarations of love for some other time and focus on getting to know your date better.

Pass up the Opportunity to Invite Her to Your Place

The first date should end with a kiss at most. Inviting your date back to your place could be too forward and move the relationship faster than it’s ready to go. Take things slow, get to know the other person, and let the relationship grow at a pace that’s comfortable for both people.

Want to find someone to go on a first date with? Contact one of our matchmakers today.


Get Started Today

Get started meeting successful Boston singles.

Call us: 617-254-3000

    X - Close