Get online dating tips, tricks, and ideas. Learn how to improve your profile, live a healthy dating life, and get a date in Boston.

Advice for Reluctant Online Daters

Last week, my mom texted me a pic of a baby.

It wasn’t a subtle hint.

I was annoyed by her hint for grandkids, but I get where she’s coming from. She wants more people in her world to love unconditionally, which is sweet but also inconsiderate because babies are expensive and scary.

Maybe for you it’s not babies, but dating (equally expensive and scary). You know you should get online-- and you’ve probably tried it before-- but you feel reluctant. You hate the idea that you’ll go on a great date and the girl won’t call you back. You hate the idea of spending a precious weeknight with someone who sneezes through the entire dinner, or comes covered in cat fur.

I get it.

There are a lot of reasons online dating sucks: there are too many people out there, it’s a lot of work, it’s easy to get addicted, it’s a huge time commitment, all the people are ugly, no one will respond to you, no one will get you, you’re moving soon anyway, you should finish your degree first...the list goes on and on.

Here’s the problem: the more weeks you live without dating, the more weeks you’ll be alone. It’s a harsh reality (seriously sucks), but it’s true. Plus, the only way to get better at dating is to keep dating.

Take online dating for what it is: a great option. You may or may not meet a match.

Here are some tips for reluctant online daters:

Remember that online dating isn't a solution

Some people, especially those who struggle to "be cool" on dates, or talk to girls at parties, see online dating as a way out.

Online dating is pretty much the same as any other kind of dating. Once you're off the site, you're dealing with real people. That means you need to be confident, comfortable in your own skin, and ready for love.

People are looking for connections. Online dating is simply a way to find them.

Choose the right dating sites

Tinder, OkCupid,, or something else? There are tons of dating sites. Which one to choose?

Here’s some advice for guys in Boston:

  • You need a mobile app. Get either Tinder, Coffee Meets Bagel, or OkCupid’s mobile app. Everyone is on Tinder, and it helps to know what options are out there. It’s also kind of fun, and allows for instant connection. The problem with Tinder is that many people aren’t looking for serious relationships. If Tinder is too overwhelming, try Coffee Meets Bagel (it sends you one match per day).

  • You need a real dating site, too. Mobile apps aren’t enough. Pair your Tinder addiction with OkCupid or OkCupid’s mobile app is fabulous.

  • Read this article on LifeHacker detailing the different sites. Again, I recommend OkCupid,, and Tinder.
  • You get what you pay for. On sites like OkCupid and PlentyofFish, women are used to THE WORST messages. Like, do you spit or swallow? What’s your favorite sex position? Women that are looking for relationships are willing to pay-- just to get off these terrible sites. I met my boyfriend on OkCupid and he is a stand up guy, get what ya pay for.

Find a woman to read your profile and be brutally honest

I realize guys are reluctant to ask other guys about their online dating profiles. Here’s where women-- your mom, sister-in-law, co-worker, old college friend, or someone else-- can come in handy.

Women have a knack for knowing what works. After all, we’re women, and we’re the ones who check out hundreds of profiles.

The trick is to ask this woman to be brutally honest. Women are really nice. We don’t want to hurt your feelings. That’s sometimes why we tell our friends they look great when we’re actually not sure. Tell her you want to know everything that’s wrong with your profile...and to not hold back.

She will help, I promise.

Decide how much time you’ll spend

People often complain that they join an online dating site and proceed to give their lives away to the art of finding a date. It’s a numbers game-- you have to send out tons of messages before getting a response (statistically, the average is 1 in 6 messages will get a response).

That doesn’t mean you should sit at your computer and spend 4 hours surfing OkCupid.

  • Make a schedule. It sounds lame, but decide to make each Tuesday “message-sending” night, or send only 2 messages per day. Give yourself a limit so you don’t make yourself crazy. And be patient-- if girls aren’t biting at first, keep at it. If you’re still having no luck, re-assess your profile, photos, and messages.
  • Get a distraction-killing web app. If you’re finding yourself checking your dating site as often as your Facebook, get ColdTurkey, which allows you to block certain websites on a schedule.
  • Disable email notifications from your dating site. If you don’t do this, you’ll be tempted to visit every day, all the time. Decide when you’re going to log in. If you’re messaging with someone, check once per day. Not more.

Pick better people to date

If you’re sending out messages like a mofo and no one replies, what’s going on?

Did you know that, as humans, we’re terrible at picking romantic partners? This is bad news when it comes to online dating.

I see tons of guys going for the hottest girls on their dating sites.Just because you and a woman are on the same site doesn’t mean you’ll hit it off, or that you stand a chance.

When messaging someone, ask yourself:

  • Can I imagine this woman hanging out with my friends?
  • On a typical Friday night, is this person doing similar things as I am?
  • Am I attracted to this person purely on a physical level?
  • Does this person seem to share similar values?

If you can’t seem to land a date, ask for help. Ask friends, family, or me (that’s what my job is), to help you pick a few prospects. Imagine they’re setting you up on blind dates.

Date multiple people (if you can)

This is easier said than done, and easier for girls than guys, but a great way to stay sane while dating is to date multiple people at once. Don’t get this twisted-- I don’t recommend that you sleep around or get multiple girlfriends. Instead, keep your options open. Don’t get too hung up one one girl before she’s ready to get hung up on you.

This is especially important for people who become extremely anxious when they meet someone they like.

Take care of your emotional health

Online dating is an extension of who you are. It’s not a solution to singledom, and you won’t be able to get a date unless your emotional health is in tip-top shape. That means a certain amount of self-love, understanding, and adaptation.

Here are some suggestions for building a healthy emotional life:

  • Read some books. Don’t read a phony book written by a pickup artist. Instead, pick up Attached: The New Science of Adult Attachment or Natural: How to Effortlessly Attract the Women You Want. I used to think self-helpy books were bogus, but I’ve actually read a bunch that give new perspectives and are truly helpful.

  • See a therapist. Therapists can help you understand what ruts you’re running into when it comes to dating, and why it might be particularly hard for you.

  • Cultivate friendships. Get out of the house and see people, whether that’s existing friends or family members.

Build an offline life, too

Part of having a healthy emotional life is building a life off the computer. Use your singledom to spend time cultivating new hobbies and interests, especially those that include other people, such as martial arts, kickball leagues, running, cycling, seeing great bands, joining Meetup groups.

If you have a rich life offline, then you’re more likely to meet people in general. Online dating is a way to open yourself up to the world’s possibilities. You need to open up on and off-line to meet the right person.

This rich off-line life will make you extremely attractive to the women you meet online.

Practice talking to girls outside of dating situations

Women are everywhere. Don’t be afraid of them. Talk to them outside of dating situations. Please, I beg you, don’t be creepy! Don't try to pick them up with suave lines. Simply make an effort to talk to women more.

  • Ask a co-worker how her weekend was. Try to sustain the conversation longer than usual.
  • Chat up a girl at a coffee shop. Don’t be creepy. Just make a joke.
  • Make a point to talk to women in appropriate places, such as at parties, bars, and while your kickball team is having an outing.

Stop being reluctant ... and be patient

I can't convince you online dating doesn't suck. In a lot of ways, it does. However, if you're not online dating, what are you doing? How will you meet the love of your life?

Remember, these things take time, so you'll need to be patient. Youre' unlikely to hit it off with your first date. If you keep at it, you'll get somewhere.

Stop being reluctant, and take these tips and get out there.

Charity's First OkCupid Date: She Gives Us The Juice!

The last time we talked to Charity she was getting ready to go on a date with a guy she'd nicknamed Vanilla.

Charity's gone on the date, and now explains how to dress, how physical to get, and how to handle the bill.

What was he wearing? Did you like it?

Vanilla was wearing khakis, and an argyle sweater with a nice shirt underneath. Business casual. I made a joke about wearing argyle to a dive bar, but he looked very nice and was much better looking IRL than in his OkCupid photos.

Did he seem nervous?

He seemed somewhat nervous at first, but I’m a decent conversationalist and we had a lot in common, plus a bit of liquid courage, and nerves were out the window.

How did you feel about the level of physical contact?

He nailed it. We greeted with a hug and he kept his arm on the back of my barstool, but left it at that. Prude? Maybe. I wasn’t trying to take him home. To be fair, he was a very nice looking guy, but I wasn’t overwhelmingly attracted to him so I was satisfied with that level of physical contact.

Were you ever uncomfortable on the date?

I really didn’t feel uncomfortable at all. We chose a good place for a first date because we had a drink, chatted for a while, shared a plate of nachos, then the live music band showed up so we watched them perform. Activities are good. Distractions and people watching are too. It was an ideal first date venue.

Did you offer to pay? How did you discuss the bill?

He took care of the bill. I offered to pay, but he said no in one hand motion with a quick “don’t worry about it.” I was partly expecting him to because it was our first date and he seemed like he would. Additionally, he lives at home. I don’t love it when that’s the case, but it doesn’t bother me either. However, I like the guy to foot the bill since he has fewer expenses than me.

What would be the best thing for the guy to do next? (Should he text you?)

I prefer to be more of the initiator in these situations. I’m not sure if I’m alone on this one, but when a guy initiates TOO much, I start to feel smothered and stop texting back. So Vanilla kept it real, we chatted for a few days and despite the great date, it fizzled out.

On to the next one!

Introducing Pierre The Prince

Today is a big day. Not only is Valentine’s Day over- phew, that’s a tough one to get through- but Frog2Prince is introducing Pierre the Prince, our resident mascot. Pierre is part of our new branding effort, and he's managed to conquer love online. Go Pierre!


Pierre the Prince is designed by Raph. Raph and I knew each other in high school, but we actually reconnected because of OkCupid. I’ve been so impressed with Raph’s fun and creative approach to graphic design. He’s shown me great stuff, and is available for hire by small businesses and startups like Frog2Prince.

Raph can introduce himself better than I can:

My name is Raph, and I've been creating art my entire life but decided to make the leap from the margins of my spiral notebooks to the big leagues of the digital world about a year ago. I think humor is fundamental to art and life, and I try to imbue my artwork with a tongue-in-cheek aesthetic.

It makes sense to have humor in comics and doodles, but I think it is also just as useful in corporate branding, logos and other “real world” design. No one wants a boring company right? Unless you do, which is totally cool. I’ll still design your graphics.


I can’t wait to show you what else Raph has designed for us- he's going to help me put Frog2Prince on the map!

If you want to contact Raph, you can send him an email or find him on OkCupid. If you want some info about professional experience, check out his LinkedIn.

I'm Just Looking for Something Casual, Can I Say So In My Profile?

By Emma Siemasko

I've been noticing a trend on OkCupid, and it's happening to me and my lady friends. A lot of guys are telling us we're pretty and soliciting us for sex. They're filling their profiles with physical characteristics they're looking for: I love blondes, I'm a boob guy, I'm looking for someone beautiful. Boys, we don't like it at all.

It's OK To Be Casual

It's not that all of us are surfing the 'net to find the love of our lives so we can settle down and have 1.5 children, but compliments about our physical appearance and direct questions about sexual preferences turn us off, even if we're using OkCupid to find a satisfying physical connection. Girls know they are attractive- they are not impressed or flattered when you tell them. We want you to tell us what you see in us, something that isn't physical.

Girls like sex, too. We're not opposed to casual flings, but we'll only agree if you go about it in the right way. Women want to feel safe, no matter the situation. No girl likes to feel like an object, like someone who is used. Make us feel special, treat us with respect, and you might find a little love alongside the pleasure you're seeking.

In the last three days, I've received a ton of messages on OkCupid telling me that I'm pretty. I DON'T CARE, BOYS. How about you ask me about something I wrote in my profile?

Real Messages From Guys on OkCupid

hi how are you doing? you are gorgeous

Hey there I'm Jack. So why are you on here?? You dont need a dating site, you are absolutely beautiful. I wanna try to make you laugh haha, so heres a joke haha. [Insert very long joke.]

You are absolutely beautiful wow I would love to chat some time and get to know you

Are you always this hot?

You have beautiful hair!

wow you're one of the most beautiful girls I've ever seen...

hey, cute pic :) that may sound strange and crazy, but I'll ask... Are u interested in having a cam slave? I'd do anything u want me to do!!! Pain, humiliation, ...... sry if I offended u by writing that message :(

Guys, it's okay to use sites like OkCupid for casual encounters, but be appropriate and considerate when creating profiles and sending messages. If you need help making a profile that gets results, or want some pointers in tailoring messages to reach the girls you want to hang out with, come talk to me. I promise I'll help you, whether you're looking for a one night stand or a wife.

Charity Prepares For Her First OkCupid Date

Meet Charity, Frog2Prince's new intern and active online dater. Charity's about to go on her first OkCupid date ever, so I asked her a couple questions.

Guys, pay attention. Charity went for this guy for particular reasons. Check back next week to find out what happened between Charity and her date!

How did you first interact with your date? Who messaged who and what did they say?

He messaged me first on OkCupid, so I checked out his profile and he seemed interesting. We shared the same college major (Political Science) PLUS he works in government for the state. His pickup line was “opposites attract”, since we’re of different political sides. Fine. He seemed able to hold an educated conversation and I wanted to keep chatting to see where things went.

What did you talk about in your messages?

We gave each other some background on each other’s lives, siblings, schooling, where we're from etc. Simple, appropriate, not weird or intimidating. Grammatically correct sentences. A little vanilla, but I've had plenty of rocky road.

How did you decide to go on a date? Who brought it up and what did they say?

After a few days of messaging through OkCupid he asked me for my phone number and we started texting. After two weeks of talking, he asked me out, I said yes, and we picked a town between the two of us to get a drink this weekend!

What made you like this guy's profile? What made you decide to go on a date with him?

I liked his profile because almost everyone had messaged me weird and inappropriate, super sexualizing and just not cool stuff (think: I'd like to make a big donation to you, Charity ;)), while he commented on a shared passion (politics). This guy seemed like he was dateable, not sketchy, and hadn’t messaged every single other girl on the website the EXACT SAME MESSAGE. (Guys, FYI we can tell when you use the same message for every girl you think is a babe. Personalize please.)

Were there particular things in his profile or pictures that you liked?

I liked how he described himself and his passions. His pictures look a tad Catfish-y, but there's one of him at a political rally that I thought was cool, plus a few selfies. What’s up with guys and taking selfies at bad angles? Especially in their cars. Please stop, it’s essentially the male duck face.

What are your expectations going into the date?

I'm not expecting to find my soul mate with this guy. Dude is totally vanilla, but as an OkCupid cherry-popper, he seems like a nice guy and a good way to start.

He's a Prince! Ted and Melissa

Hey Froggies,

Meet Melissa, a girl that met her boyfriend on eHarmony, and friend of mine from college. I reached out to Melissa about how she met her current Boo- she answered a few questions for me via email. She's known for her cheesecake brownies- she probably makes them for Ted!

Take notes, boys:

Who are you?

I’m Melissa, I’m an urban planner in Boston, but I’m originally from Maine. I’m 25.

Who is he?

He is Ted, a 27 year old high school science teacher and a card-carrying nerd.

Why did you decide to go on a date?

I decided to go on a date with him because he asked! But, I messaged him first, for which I will ALWAYS take credit. He was so discouraged about online dating that he was no longer sending messages to anyone.

What spoke to you in his profile?

I enjoyed his travel pictures, how happy he seemed in all these photos (his students call him Mr. Chuckles), and his responses to the eHarmony questions. I just had a sense of wanting to know more about him.

What did you talk about while you were messaging?

We talked about what we liked to do and our family and friends. Each message seemed to be better than the previous one. I was hoping he’d ask to meet me, and he did---two and a half weeks after I sent the first message.

What happened on your first date?

Our first date was at the Paramount on a Sunday morning. I was early. I waited in the very long line and saw him come through the door. He was tall, dark, and handsome, and dressed nicely in a button down shirt. I managed to say, “You must be Ted?” and prayed I didn’t look as nervous as I was.  During our date I spilled my drink all over our table, forgot everything he mentioned in our messages, including where he went to college, and earned a self-assessed D-. Somehow, he left thinking I was adorable and looking forward to the next date.

What are you guys doing now?

After dating for over a year in the same city, then doing long-distance for eight months, we’ll be living in the same city again in three weeks! We’re excited about our future together!

The Frog2Prince Pond Isn't Frozen- A Sister Site, Social Media, and Hawaii

By Emma Siemasko

Hey Froggie Dudes and Frogettes.

I haven’t posted to the blog in awhile, so I’m checking in to tell you what’s going on at the Frog2Prince pond.

Frog2Prince is getting a lot of attention- I’ve heard from a lot of users about their ideas. I hired an intern---who you’ll meet in the next blog post---and made a New Year’s resolution to help YOU date in 2013. Based on your feedback I realized that Frog2Prince should extend beyond OkCupid to other dating sites and I’ve done a number of edits for users on Match, eHarmony, and OurTime.

I’m Working on Duck2Swan, A Sister Site

The ladies are looking for profile transformations, just like their counterparts, so Duck2Swan is in the works. The sister site will launch in no time, so guys, watch out for hungry swans swimming in your ponds!

We are also working on a redesign for Frog2Prince so it will be as handsome as your profile. We want to have a fun logo, so if you’re an illustrator or designer, please get in contact.

You Can Now Follow Us On Twitter and Like Us on Facebook

Frog2Prince now has a presence on Facebook and Twitter, so you can check for updates about what we’re doing. The social accounts are informal- follow up for fun stories and tips, even if you're already in a relationship.

The Frog2Prince Cofounders Went to Hawaii

I took a vacation with my boyfriend to Hawaii, where we doled out online dating tips to coworkers and friends. Thanks to good dating profiles, we wound up on a romantic trip in Maui. A mathematician complimented me on my Michael Kors iPhone bag- what a way to flirt!

The best part of going to Hawaii in January wasn’t the humpback whales, the sea turtle snorkel, or the sunset sail- the most sunshine-y, happy part was going with my boyfriend who I met on OkCupid. I want people to have what we have- a loving relationship that’s fun, exciting, and satisfying. That’s why I want to help you refine your profile- check out my packages! I'm still offering a free profile grade.

Resist the Stigma: Normal People Date Online

WOW. The overwhelming support that Frog2Prince received on opening day was spectacular, so thank you.

I was happy to see so many girls interested in the packages offered by Frog2Prince, even though we're catering to men. Both women and men can submit their profiles through Frog2Prince. (Pst...a sister site is in the works!)

Online dating isn't romantic

Last night I discussed online dating with a few friends. One of the single guys remarked that he wants to meet someone the "old-fashioned way."

"Don't we all?" said a girl friend, "But that just isn't happening."

I told them that I'd seen a lot of friends meet people in the "old-fashioned way" while they were online dating. Being online forces you to put yourself out there, helps you define what you want in a significant other, and challenges you to take charge of your love life. I know that sounds corny and a little self-helpy, but many resist online dating because of the stigma attached to it.

Online dating isn't romantic. It requires you to stare at a computer screen like a programmer, miles away from your potential mates, unable to defend yourself. The only romantic part of this is that you're probably in your underwear. Even still, going on dates can be FUN. REALLY. I PROMISE.

Normal people date online

Girls are worried about sketchballs, guys are worried about girls being 30 pounds heavier than their photos. I think these are just excuses-- NORMAL PEOPLE DATE ONLINE.

Resist the stigma, put yourself out there, create an online dating profile, and Frog2Prince will do our best to help you meet some great people on fun dates. Let us help you!

Let's celebrate the launch of Frog2Prince

Hello toads, frogs, and other amphibians! Welcome to Frog2Prince.

Online dating is tough, but now Frog2Prince can transform you from a warty little bullfrog to a tight-wearing prince. We're here to help you make girls swoon, let down their hair, and let you kiss them.

I started this site because I was constantly giving men (and women) feedback about their online dating profiles, specifically on OkCupid. I spent time on the site myself, which is how I met my boyfriend. He helped me get Frog2Prince off the ground.

This blog will be a resource to singles as they try to negotiate the difficult landscape of online dating. We'll give you tips and tricks about how to message girls online, what to wear on dates, whether or not you should pay, and how to get more responses.

Trust me! I know what works!

I'm offering three packages, catering to men who need a little assistance in understanding how their profile comes off to women. You can sign up for them here.

The Tadpole $25 The tadpole package includes a custom online dating profile analysis. We include photo critiques, detailed suggestions, and edits for grammar and spelling.

The Prince $100 Our Prince package is a complete consultation with Frog2Prince. We'll edit your profile, help you with messaging, have a 15-20 minute pre-date Skype session to assist you in choosing a cool date location and picking a hot outfit.

Profile Grade FREE For a limited time, our profile grade is free. We'll assess your OkCupid profile based on four categories: Personality, Photos, Spelling/Grammar, and whether or not we'd be willing to go on a date with you.

I'm excited to provide tips to single men about how to snag their princesses!

xox Emma