3 Ways to Keep the Conversation Flowing On a First Date

You did it! You’ve met someone great on Plenty of Fish, had amazing conversation online and are ready to meet in person, awesome. Unfortunately, sometimes the difficult parts about dating aren’t even in finding a person, but finding how to actually connect with another person. Witty banter, charm, and a relaxed flow of conversation are not things that can be faked IRL. Often times – even when you know you would hit it off with your date – your nerves inhibit you from carrying on a thriving conversation. But, here’s a secret, you can be yourself on a first date despite those inevitable nagging nerves. Down with the awkward silence!


The easiest way to speak freely is to speak about things that you like. Duh, right? I used to keep a self-serving question in my dating arsenal that would help me determine further interest in my date; It was arrogant, but worked. I would either ask “what are reading right now?” or “what are you listening to right now?” Books and music are topics of interest to me, finding out what my date is interested in helped me relate to them. If things are going well and the other person had an answer (probable) it would spawn another conversation and another and another.

Don’t feel shy to give anecdotes about your life. The idea is to get to know each other; you probably aren’t talking about yourself as much as you are stressed about talking about yourself too much. Giving specific details to the plot of a story you’re telling will create imagery that in turn helps the other person engage with you. Extra points if the story happens to be fun. Laughing is a great way to ease up.


Just as it’s easiest for you to speak about your own experience, it’s equally as simple for someone else to do the same, give them a chance to. Listen when your date is talking. No, not that half-listening we all enter into once in awhile where we are preparing the next thing we’re going to say while the other person is still speaking. Really listen. When you genuinely listen to another person speak it provides the opportunity to naturally fall into a more empathetic listening mode. Also, ask questions. Not only will this help in keeping the conversation rolling, you will learn so much about your date. And, isn’t that the point?


Dating should always be fun; make comments about your surroundings, poke fun (with caution) at yourself and your date, laugh, acknowledge that you’re nervous – it’s all ok. Remaining calm, cool and collected is a feat easier said than done, I know. Dating can be intimidating, especially when you feel there might be a spark. A good way to avoid getting caught up in your thoughts, and acting out of character on a first date is to remember: You are interesting! Take a second to give yourself a confidence boost. This person is on a date with you.

Simple Tips to Elevate Your Dating Game

Between work, hobbies, family and friends, it can be hard to find time to date. But when you finally get some free time, you can meet people anywhere these days. There is no doubt that asking someone out can feel gut wrenching, but once they’ve said yes, the rest is a no-brainer. The most important thing to remember while dating is to keep an open mind. Bad dates might happen, and probably will happen, but they’ll only help you figure out what you want and don’t want in a partner. Throughout the process you’re going to have some questions, and thankfully, others have been in your place and have advice to help build your confidence and success in the dating world.

Is it wrong to text or call before the first date?

Before the big date, make sure you’re still actively communicating with your match. There is nothing worse than being ghosted before the first date even starts. While the two of you are chatting, make sure you figure out each others interests. This will help determine where your first date will take place. First impressions go a long way, so we recommend choosing a public location that will allow you to feel comfortable, and act your natural self. If you’re having trouble deciding where to take your date, check out these 20 Great First Dates for some inspiration.

What should I wear?

There is no need to stress when picking out an outfit for your date. Determining the location of the date is the stressful part, so figuring out what to wear should be stress-free! If you’re feeling unsure about what to wear, pick out a couple options and ask for some opinions. What else is Snapchat good for these days? Your friends won’t let you down!

When figuring out what to wear, make sure you are comfortable in whatever you’re wearing. There is nothing worse than sitting for hours in an uncomfortable pair of pants or sweating under multiple layers. If you feel confident in what you’re wearing, you’ll be able to act comfortable around your date. If your first date takes place during the day, or err on the side of wearing something casual (but not too casual!). For the ladies, we recommend wearing a fun colored sweater, such as this one, with a pair of skinny jeans. Throw on your most comfortable pair of booties, and you’ll be ready for your date! For the men out there, try wearing a pair of stretch jeans with a nice long sleeve shirt. Add a pair of chukka boots to elevate your casual look.

If your date takes place in the evening, try to figure out as many details about where you’re going before picking out an outfit. If the date is a surprise, try to give the other person as many specifics about the location. There is nothing worse than showing up somewhere under or over dressed for the occasion. For the women out there, you can never go wrong with a great pair of black jeans. Dress your jeans up with a black blouse with some accent jewelry, or a leather jacket. For the gentlemen, spruce up your dark wash stretch jeans with a classy dress shirt. Add a blazer on top for a dressy casual look.

Is dating etiquette still a thing?

Dating etiquette is by far the most important aspect of a first date. Looking good in your outfit shouldn’t be the only reason to “wow” your date. Etiquette is by far the most crucial aspect to a first date, and when taken into consideration is likely to increase your chances of getting a second date. There certainly will be nerves at the beginning, but don’t let that be a reason to forget your manners. One of the biggest things to think about is disconnecting from your phone. It can be hard, but we highly recommend putting your phones away altogether to avoid any temptation to use it. There is no worse feeling than being on a date when the other person whips out their phone to check out their Instagram feed or Snapchat a picture of their dinner – don’t be that person. Make sure you are engaged in the conversation. Eye contact and good conversation can go a long way! Check out how to tell if your first date is going well here.

The first date ends, now what?

Like mentioned before, always remember to keep an open mind while dating. You might not feel a connection with someone after the first date, and that’s okay! There is no reason to feel bad or upset. It’s a learning experience. The best thing you can do at that point is to be honest with the other person. Don’t agree to a second date if you’re just going to ghost them or make up an excuse in the end. They’ll appreciate it and you can build up your confidence in making the right dating decisions.

Lastly, there is always the debate of waiting a few days to text your date or to contact them right after your first outing. If the date was a success, don’t let any doubts cross your mind. Let them know that you had a great time! Don’t feel timid, and confidently plan that second date. If both parties are interested, the other person should offer to make the plans this time. And if that’s you, don’t stress. After all of the great conversation from the first date, planning a second should be easy!

What’s Next After Valentine’s Day?

February 14th creates mixed emotions for people: some celebrate their love for their partner, while others celebrate being single with friends, some enjoy the day alone with wine and ice cream and there are some don’t celebrate at all.

But what happens after Valentine’s Day?  Where do we go from Cupid’s celebration?

Here are some suggestions to put a spring in your step:

1) Pamper yourself.

It’s super important to have “me time.” It can be anything that gets you feeling spoiled.  Take a break to curl up and read that book that you keep eyeing but never get a chance pick up.  Put the headphones on to listen to the tunes that you have recently downloaded.

Have a spa day. If you don’t have time for an entire day, maybe a facial or just a pedicure. Also a hot rock massage helps melt away any stress that you might be holding in from the winter blues. It’s all about taking care of yourself.  

2) Take a class or volunteer.

Spring is the perfect time to start something new.  If there is a class on your bucket list, move it over to your accomplish list. It doesn’t have to be a full semester course, there are one night classes or classes for 6 weeks.  There are all kinds of classes out there: from cooking to photography; music to languages.  Have a look at the local colleges and any online programs in your area.  

Volunteering is all about your passion. It also flexible to work around your schedule.  The opportunities are everywhere: from dog walking at the local shelter, to reading to seniors to helping out at events. Whatever your interests are, there is a volunteer job that matches.

Both of these activities promotes self-confidence and is also a great way to meet people with similar passions.

3) Spend time with friends and family.

Nothing bond friends and family like a potluck or an afternoon out at the bowling lanes. Dust off pictionary, charades or the family favorites to spark healthy competition.  It’s relaxing and fun to be around people that have been with you through thick and thin. Enjoy the time to just release stress and be yourself.  

4) Enjoy the great outdoors.

There is something about Mother Nature that is refreshing and invigorating. For those who may not be hiking enthusiasts, there is lots to do outside.  In the winter, there is snow shoeing and skiing, also there are some local attractions that are opened all year round.  You could also play tourist for an afternoon and explore your town on foot.   The goal is to disconnect from the everyday routine to help reset and energize.

5) Spring cleaning.

Nothing helps moving on better than letting go.  Take on that one closet that you look away from every time you walk by it. Donate the clothes that you have not worn in a year to a non-profit group.  Recycle old electronics that are sitting around collecting dust. There is a sense of accomplishment and closure when you clear things out of your home that you no longer need.  

Valentine’s Day may be over for another year, some enjoyed the love and passion of it while others maybe not so much. Spring is just around the corner and it’s the perfect time to release, energize and let go.

Love Lessons Learned From Broad City’s Fourth Season

As we all sit in mourning because the recent season of one of the most brilliant comedic programs – Broad City – has come to an end, it’s imperative to reflect on the lessons learned alongside the protagonists, Abbi and Ilana. The fourth season of Broad City, which aired in September on Comedy Central, took the regular comedic tone of the show and turned it on its head; more character growth, further topical discussion, and of course, life lessons. Each season, viewers garner a deeper insight into Abbi and Ilana’s relationship. This season, within the heavy supply of empowering material, Abbi and Ilana (the creators, not the characters) were sure to throw in some low key lessons of love as well – enthusiastically leading us to explore them.

Ep. 02: Twaining Day

Lesson: Don’t force something that isn’t there.

Man, I feel like Abbi and Trey’s secret turned not-so-secret relationship just started. Though Trey was smitten with Abbi, the two didn’t share the same level of infatuation. Abbi confused lust for romantic longing, inevitably creating an awkward situation between her and the Garden State superfan. Their re-run relationship was bound to fail. You can’t force feelings.

Ep. 03: Just the Tips

Lesson: There is never a need to rush into anything.

After being accused of “not being a relationship person,” Abbi’s insecurities lead her to mentally jump into a relationship that isn’t there. After seeing Mike for a mere 6 days, Abbi convinces herself that she is not only in a long term relationship, but is now a relationship guru. In this episode we learn that you never need to rush into anything romantically. Also, giving relationship advice when you’re fresh into one can sometimes be pretty dang creepy.

Ep. 04: Mushrooms

Lesson: Respect your body’s process.

When Ilana is faced with her ideal situation – being approached by an open minded couple for a threesome, of course – her body doesn’t respond the way she wants it to; she can’t figure out why her body isn’t quite as excited about the experience as her mind is. After some trials (and tribulations), Ilana and the couple come to realize that it’s not going to work. This is just another subtle reminder to trust your body; it knows what’s up, sometimes before your mind does.

Ep. 06: Witches

Lesson: Celebrate your sexuality.

There is something affecting Ilana which is preventing her from performing sexually, the way she is used to. After a visit with a sex therapist it is revealed that the source of her sexual angst lays in the results of the American presidential election. Sexuality shouldn’t be a realm of negativity; never let anything big or small stand in the way of your sexual pleasure!

Ep. 08: House-Sitting

Lesson: If a situation feels hazardous, TRUST YOUR INSTINCTS.

Abbi reconnects with one of her high school teachers, making her feel a tinge uneasy. The two agree to spend the evening together on a first date of sorts, but along the way red flags are revealed about the teacher which Abbi questions, and ignores. If you feel uneasy, always trust your gut.

Ep. 08: House-Sitting

Lesson: Check in with your SO; treat the relationship as it grows.

Lincoln + Ilana 4ever! Our favourite TV dentist by day, pasta connoisseur by night,  Lincoln and half of BC’s witchy heroine team, Ilana, have finally solidified the bounds of their enigmatic connection. From what we have gathered in the first three seasons of Broad City, Ilana doesn’t have much experience in the realm of serious relationships (aside from her friendship with Abbi). As such, when she is finally able to call Lincoln her “boyfriend” she takes it on and wears it as a badge of honour, embracing it probably too fully. In one night they manage to go from the relationship highs (dressing up, showing each other off), to the getting comfy stage (a farting contest – more or less), to the lows (fear of being too comfortable, lack of sex). It’s great that Ilana is at the ready to recharge the relationship by being creative – even if it is unwarranted. But, Lincoln’s advice is what we’re here for. He reminds her that it’s important to check in with one another and take things step by step, at your own pace. That Lincoln, so wise.

From Work to Date Night in 3 Simple Steps!

Going straight to a date from work is equally exciting and daunting—exciting because dates can bring new possibilities into our lives, and daunting because of the never-ending question of what to wear. There is usually a quick time turnaround between the two commitments. As a busy woman, it’s important to make the most of your precious time. Use these three steps to quickly turn your no-fuss business meeting dress into a flirty meeting-for-drinks outfit.

Plan Ahead

When you’re trying to squeeze date night into an already-busy work day, you can save yourself a lot of indecisiveness and stress by planning ahead. Take some time the weekend before to decide what you’re going to wear to work. This may seem like an unnecessary tip at first glance, but if you don’t find an outfit you love, you’ll have time to shop online or head to the mall to make a quick purchase. Consider shopping at an online (or offline) consignment shop to find a one-of-a kind, date-ready piece on a budget. When the morning rush comes the day of your date, your future self will thank you for having an outfit ready. You’ll begin your day with a winning mentality that will breed confidence into your morning. Sounds like the perfect way to walk into a busy day that includes a date night!

Start Neutral

When choosing your outfit, you want something that’s work appropriate but will serve as a great base for your date — assuming you don’t want to lug around a bag of clothes to change into when the workday is over. Your best bet is a dress in a neutral color. Whether you prefer a palette of black, navy, camel, grey or white, pick a dress with a classic silhouette that makes you feel comfortable and confident. Steer away from any necklines or hemlines that might not fly at work. (If you’re questioning whether it will be appropriate, chances are it’s not.) Worried about looking too plain or business-y? Don’t fret. A neutral dress is the perfect blank canvas for the next step.

Pack Accessories for Later

Once you have your neutral base, you can transform it with personality-packed accessories after 5 p.m. hits. Swipe on a pop of bright lipstick, don a pair of bold earrings or switch out your pumps for a showy statement heel. The right accessories can take any outfit up a notch and make it date night-ready in a jiffy. Take this opportunity to use jewelry, coats, scarves or shoes to infuse your personal style into your date night outfit. Have fun with it, and express yourself!

Dressing for a chock-full schedule that includes running from work to a date night can be overwhelming, but with these dressing guidelines and the magic tip of planning your outfit ahead of time, it can be fun.

Guest Post Contributed by thredUP.