Single  in  the  City’s  HOW  TO  Guide  
 
How  to  Impress  Your  Date  to  Get  the  
Second  Date  
 

 
Chapter  Summary:  
Chapter  1:  
It  All  Starts  With  YOU:  Self-­‐confidence  Booster  Tips  
 
Chapter  2:    
The  inside  scoop  into  the  male  and  female  psyche:  What  
they  are  really  looking  for  in  a  partner  
 
Chapter  3:  
Flirting  and  Approaching:  How  To  
 
Chapter  4:  
How  To  Ensure  You  Get  The  Second  Date  
ü Single  in  the  City’s  First  Date  10  Point  Body  Makeover  
Checklist  
ü 20  Things  You  Should  Never  Do  On  A  First  Date  
ü First  Date  Reminders  
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

  2  
  
 
In  a  world  where  the  way  we  meet  people  and  date  has  evolved  over  the  years,  
getting  to  a  second  date  has  become  overwhelming  and  difficult  for  some.    The  
perception  of  dating  is  that  it  is  increasingly  complicated,  so  much  so,  that  when  
your  date  calls  you  on  the  phone,  you’re  in  shock  and  don’t  know  what  to  say  or  do!    
Text  messages  and  emoji’s  are  left  to  interpretation.    Now  with  so  many  ways  to  
date  and  meet  people,  all  the  interpretation  and  overanalyzing  comes  with  it.    You  
may  even  be  left  with  the  idea  that  meeting  someone  in  person  is  like  capturing  the  
unattainable,  proverbial  unicorn!      
 
What  if  I  told  you,  dating  can  be  simple  and  easy?      
 
Single  in  the  City’s  HOW  TO  Guide  on  How  to  Impress  Your  Date  to  Get  the  
Second  Date,  brings  attention  to  what  most  daters  are  missing  in  order  to  have  
successful  dating  lives.    What  used  to  seem  obvious  and  common  sense  for  some,  
has  become  saturated  with  dating  interpretation  and  overanalyzing.      
 
As  we  all  know,  if  we  can  get  to  that  second  date,  there  is  a  higher  likelihood  of  your  
dating  relationship  evolving  into  something  more  serious.    This  guide  is  designed  to  
break  down  what  you  need  to  know  in  order  to  be  successful  in  your  dating  life  and  
score  that  second  date.      
 
Again,  where  most  dating  books  go  into  games  and  interpretation,  our  goal  is  to  
bring  our  Single  in  the  City  daters  back  to  your  primal  instincts,  while  implanting  our  
recommended  core  dating  beliefs  and  strategies.      
 
Where  does  your  dating  life  begin?    With  YOU.    Let’s  get  started.    
 
 
 

 
 
 
 
 

  3  
Chapter  1:    
It  All  Starts  With  YOU:    Self-­‐Confidence  
Booster  Tips  
The  success  of  your  dating  life  starts  with  you.    As  overwhelming  as  that  may  sound,  
it’s  really  quite  positive  for  you.    Because  your  dating  life  starts  with  you,  you  have  
the  ability  to  look  within,  assess  what  you  need,  find  it  and  put  your  best  foot  
forward  in  order  to  attain  it!  

Self-­‐confidence  is  the  #1  most  important  trait  for  attracting  a  partner.    Confidence  is  
not  just  based  on  how  you  look  on  the  outside  but  how  you  feel  on  the  inside.    Self-­‐
confidence  is  the  belief  in  yourself  and  your  own  abilities.    When  you  
wholeheartedly  love  yourself  and  believe  in  yourself  first  and  foremost,  that’s  when  
the  dating  magic  begins  to  happen.      

For  some,  self-­‐confidence  comes  easy  but  for  most,  the  path  to  self-­‐confidence  can  
be  a  bumpy  road  and  is  in  reality  a  life  long  journey  of  self-­‐discovery.  How  you  
regard  yourself  has  a  huge  impact  on  how  others  view  you.  The  more  self-­‐
confidence  you  have,  the  more  likely  you  are  to  be  successful  in  fostering  healthy  
and  long  term  relationships.    

For  the  purpose  of  this  book,  we  wanted  to  focus  on  the  tangible  things  you  can  do  
TODAY  to  immediately  improve  your  self-­‐confidence.    With  that  being  said,  if  you’re  
in  need  of  support  to  help  build  your  self-­‐confidence,  it  never  hurts  to  seek  out  
support  within  your  family  and  friend  network  or  even  by  reaching  out  to  an  
objective  party,  such  as  a  counsellor  or  date  coach.  

Here  are  a  few  self-­‐confidence  booster  tips  to  get  started:  

1. Use  positive  affirmations:    Affirmations  are  powerful  statements  that  you  

believe  to  be  true.    Repeating  positive  affirmations  in  your  daily  life  instead  
of  focusing  on  the  negative  can  assist  you  to  reframe  your  mind.    Pay  close  
attention  to  your  self-­‐talk,  are  you  as  loving  and  compassionate  towards  
yourself  as  you  are  to  others?    *See  below  for  some  examples  of  positive  
affirmations  you  can  start  with  today.    
2. You  come  first:    YOU  are  the  most  important  person  in  your  life,  treat  
yourself  well.  Incorporate  healthy  eating  into  your  routine  and  regular  
exercise.    Exercise  in  particular  releases  endorphins  which  help  you  to  feel  
happier  and  healthier.  Also,  be  kind  to  your  body  and  rest  when  it  needs  it.    
Adjust  your  schedule  if  you’re  struggling  with  burnout.    Listen  to  your  body.    
3. Do  things  that  derive  passion  and  joy  from  your  life.    Is  there  a  hobby  that  
you  could  turn  into  a  career?    Have  you  ever  tried  volunteering  for  a  good  
cause?    Do  things  in  life  that  make  you  feel  good,  sometimes  that  is  even  

  4  
 giving  back  to  others.  
4. Dress  to  impress:    When  you  feel  you  look  good,  natural  self-­‐confidence  is  
emitted.    Although  there  are  some  days  when  leaving  the  house  in  sweats  is  
warranted,  most  of  the  time,  you  don’t  feel  good  about  yourself  when  you  do  
it.    As  crazy  as  it  may  sound,  taking  the  time  out  of  your  busy  schedule  to  
update  your  look  when  you  walk  out  the  door,  can  have  a  big  effect  on  your  
self-­‐confidence.    Why  risk  a  run  in  with  that  crush?      Feeling  challenged  in  the  
looks  department?    Have  someone  help  you  out  with  your  wardrobe  if  you  
feel  that  you  don't  have  a  sense  of  style.  There  are  plenty  of  stores  that  have  
sales  clerks  that  will  help  you  find  what  looks  best  on  you.  This  also  goes  for  
a  nice  fragrance.  For  men,  let  the  girls  behind  the  counter  help  you  find  a  
suitable  scent  that  will  melt  the  object  of  your  affections  heart.  A  man  or  
woman  that  smells  good  can  be  irresistible.  
5. Practice  makes  perfect:    When  it  comes  to  dating,  practice  really  does  make  
perfect,  and  with  practice  comes  self-­‐confidence.    The  more  dates  you  go  on,  
the  easier  it  becomes.    Conversation  starts  to  become  easier  and  nerves  tend  
to  subside.    Not  sure  where  to  start?  Approach  those  prospects  on  a  more  
regular  basis.    See  that  hottie  in  the  grocery  line?    Say,  “Hi!”    What  do  you  
have  to  lose?  Sign-­‐up  to  attend  a  speed  dating  event  or  hire  a  Matchmaker  to  
do  the  picking  for  you,  there  are  so  many  supports  out  there  to  assist  you  in  
building  your  dating  confidence.    
   
*Below  are  5  positive  affirmations  that  will  support  you  to  change  not  only  in  your  
dating  world,  but  hopefully  help  to  transform  the  way  you  view  yourself  within  your  
daily  life.  Make  sure  to  repeat  these  affirmations  on  a  daily  basis.    The  idea  is  that  
that  a  positive,  consistent  mind,  will  help  to  create  your  positive  reality.    

♥ I  am  a  great  catch  and  someone  would  be  lucky  to  have  me!  
♥ Nothing  is  impossible  and  life  is  great!  
♥ I  have  a  powerful  belief  in  myself!    
♥ I  am  a  success  in  all  that  I  do!  


 

 
 
 
 
  5  
Chapter  2:    
The  inside  scoop  into  the  male  and  
female  psyche:  What  they  are  really  
looking  for  in  a  partner  
Before  we  delve  into  what  your  future  partner  is  looking  for,  let’s  do  a  quick  
inventory  on  what  you’re  looking  for.    

Knowing  what  you  want  and  what  you  don’t  want  in  a  partner  is  extremely  
important  in  the  “picking  process.”  

Really  identify  your  must  have’s  and  your  deal  breakers  before  you  even  begin  to  
look  for  potential  partners.    What  are  characteristics  or  habits  that  you  would  
absolutely  not  be  able  to  overlook  in  a  partner?  For  example,  if  you  know  you  could  
never  be  with  a  smoker  long  term,  don’t  pursue  a  smoker.    If  you  want  to  have  
children  one  day,  dating  someone  who  is  not  sure  if  they  want  children  at  all,  is  not  
what  you’re  ultimately  looking  for.    

Knowing  what  you  want  in  a  partner  and  being  clear  on  those  characteristics  and  
traits  will  help  you  identify  who  that  partner  is  for  you.      

Now  that  you  have  thought  about  what  you’re  looking  for  in  a  partner,  let’s  look  at  
what  your  potential  partner  is  looking  for.    

FOR  THE  WOMEN:  What  men  typically  look  for  in  a  partner.  

1. She  has  a  “girl  next  door”  in  her.    Men  love  a  woman  who  can  dress  up  for  a  
nice  evening  out  but  is  also  comfortable  enough  with  herself  to  take  all  that  
makeup  off  and  chill  out  with  him  in  a  more  natural  setting.  With  that  being  
said,  be  yourself,  the  right  man  for  you  will  fall  for  who  you  are,  not  who  you  
are  trying  to  be.    They  key  is  being  comfortable  enough  with  yourself  to  
be  yourself  with  a  man.    
 
2. She  is  caring  and  nurturing.  A  man  likes  to  feel  needed,  nurtured  and  cared  
for.    As  old  school  as  that  may  sound,  when  a  man  can  let  his  guard  down  
enough  to  let  you  take  care  of  him,  that  is  when  you  know  he  trusts  you.    How  
do  you  show  him  that  you  care?    Show  him  that  you  care  by  listening  when  
he  needs  an  ear  and  by  putting  in  the  time  and  effort  to  make  the  relationship  
work.    Men  can  be  just  as  insecure  and  “needy”  as  women  can  be,  it’s  
important  for  a  man  to  feel  as  needed,  as  he  is  cared  for.    
 
3. She  cooks.    The  true  way  to  a  male  heart  is  through  his  stomach.    I  can  attest  

  6  
 to  this,  I've  always  cooked  meals  for  my  boyfriends  and  each  and  every  one  
of  them  loved  it.  Men  really  appreciate  the  effort  when  it  comes  to  a  meal,  
even  if  you  aren't  the  best  chef  in  the  world.  
 
4. She  is  the  best  version  of  herself/Physical  attraction:  Initial  physical  
attraction  is  important  to  men,  if  they  aren't  attracted  to  you;  the  
relationship  likely  has  no  chance.    I  have  yet  to  meet  a  man  that  has  
confirmed  he's  not  looking  for  a  women  he  is  attracted  to.    Of  course,  beauty  
is  in  the  eye  of  the  beholder,  you  don't  have  to  be  a  supermodel  but  when  you  
walk  out  that  door,  I  recommend  you  embrace  the  best  version  of  you.    You  
never  know  when  or  where  you  will  meet  someone  when  you're  single.    
Besides,  when  YOU  believe  you  look  and  feel  good,  others  feel  that  from  you  
too!  
 
5. She  has  a  softness  about  her:  A  woman,  who  is  always  on  the  offensive,  is  a  
tough  woman  to  crack  and  get  to  know.      A  woman  who  has  softness  does  not  
feel  the  need  to  go  to  battle  about  everything  and  can  handle  a  difficult  
situation  with  an  air  of  calmness.      She  is  secure  in  herself.    
 
6. She  can  be  spontaneous:    Most  men  are  not  planners  and  tend  to  do  
everything  last  minute.    I  know  this  because  of  the  speed  dating  events  I  
facilitate.  Women  tend  to  book  further  in  advance  and  most  of  the  men  book  
the  day  before,  or  day  of  the  event.    This  is  why  speed  dating  events  are  
sometimes  unpredictable,  you  never  know  if  you're  going  to  have  a  full  
house,  until  the  end.    Men  are  attracted  to  women  who  are  not  always  
regimented  and  structured.    Of  course  there  is  a  time  and  place  where  
structure  makes  sense,  especially  when  it  comes  to  children.    With  that  in  
mind,  a  woman  who  can  roll  with  those  last  minute  plans  here  and  there  is  
very  attractive  to  a  man.  
 
7. She  is  happy  with  herself  and  knows  what  she  wants.  I've  heard  countless  
men  tell  me  how  the  women  they  are  dating  don't  know  what  they  want  and  
it’s  a  turn  off.    It  is  extremely  important  to  explore  what  makes  you  happy  
first  and  foremost.    What  derives  passion  for  you?    When  are  you  at  your  
happiest?    What  qualities  are  you  looking  for  in  a  partner?    When  you  have  an  
understanding  of  who  you  are,  what  you  are  looking  for  and  what  makes  you  
happy,  there  is  a  sense  of  confidence  and  peace  that  exudes  from  the  inside  
out.    
 
8. She  is  a  compromiser.    Stubbornness  is  not  an  attractive  quality.    Having  
empathy  and  being  open  enough  to  take  into  account  someone  else’s  opinion  
is  important  to  men.    
 
9. She  has  a  sense  of  humour.    A  sense  of  humour  is  such  a  turn  on  for  men.    
Having  a  sense  of  humour  means  that  you  can  see  the  bright  side  of  most  
situations  and  can  poke  fun  at  yourself  once  in  a  while.  

  7  
  
10. She  can  tap  into  her  vixen  side.    Are  you  comfortable  with  your  sexuality?    
Men  are  intrigued  by  women  who  are  comfortable  with  who  they  are  and  can  
let  go  once  in  a  while,  in  and  out  of  the  bedroom.    

Now,  FOR  THE  MEN:  What  a  woman  looks  for  in  a  man.    
 
1. He’s  honest.    When  you  lie,  you  run  the  risk  of  breaking  that  trust.  Once  the  
trust  is  broken,  it’s  very  difficult  to  get  it  back  and  can  
cause  tremendous  problems.    A  woman  appreciates  full  disclosure  and  
openness  from  a  man.    
 
2. He  is  trusting  and  secure  with  himself.    On  the  other  side,  you’re  the  non-­‐
jealous  type  who  doesn't  question  her  when  she  wears  that  top  or  walks  out  
that  door  to  go  out  with  friends.      A  man  who  comes  off  as  clingy  or  desperate  
runs  the  risk  of  driving  their  object  of  their  affection  away.    
 
3. He  is  intelligent  and  can  have  an  intelligent  conversation.    Intelligence  
does  not  necessarily  mean  book  smart,  ones  attraction  to  intelligence  can  
range  from  their  social  intelligence  and  their  ability  to  interact  well  with  
others,  to  being  able  to  hold  down  an  intellectual  conversation  on  a  date.    If  
you  typically  run  out  of  things  to  talk  about  on  a  date,  try  keeping  updated  on  
what  is  going  on  in  the  world  around  you;  listen  to  radio,  watch  the  news,  
read  the  paper  or  online  publications.  
 
4.  He’s  confident.    A  man,  who  is  comfortable  in  his  own  skin,  takes  ownership  
of  who  he  is.  
 
5. He  goes  after  what  he  wants/goal  oriented.    Women  are  very  attracted  to  
a  man  who  knows  what  he  wants  and  makes  it  happen.    A  man  who  is  goal  
oriented  can  be  extremely  sexy.      
 
6. He’s  a  gentleman.    You’re  a  man  who  can  pick  up  the  phone  to  ask  her  on  a  
date  instead  of  being  insecure  and  afraid  of  rejection.    One  of  the  biggest  
pieces  of  advice  I  give  men  is,  pick  up  the  phone,  be  different,  stand  out  from  
the  rest.    Even  holding  a  door,  pulling  out  her  chair;  these  little  gestures  go  a  
long  way  with  a  woman.    
 
7. He’s  a  protector.  Women  turn  to  men  to  feel  safe  and  protected.    The  safer  a  
woman  feels  with  you,  the  more  she’ll  respect  you  and  want  to  be  around  
you.  
 
8.  He’s  health  conscious.    A  man  who  takes  care  of  his  physical  well-­‐being  is  
very  attractive  to  a  woman.    This  includes  a  man  who  takes  pride  in  the  way  
he  looks  and  carries  himself.  

  8  
  
9. He’s  generous.    This  does  not  mean  that  you’re  necessarily  someone  that  
buys  her  gifts  all  the  time  but  that  you’re  generous  and  giving  in  general.    
When  you’re  generous,  you’re  not  afraid  to  lend  a  helping  hand.  
 
10. He  has  a  great  sense  of  humor.    Your  ability  to  laugh  and  laugh  with  others  
is  highly  attractive.    If  you  can  make  her  laugh  a  lot,  you’re  already  a  head  of  
the  game.  
 
11. He’s  easygoing.    Although  this  is  a  trait  that  most  individuals  look  for  in  a  
partner,  as  a  man  you’re  ability  to  adapt  to  a  woman’s  needs  is  very  sexy.    
 
Now  that  you  are  clear  on  what  your  potential  future  date  is  looking  for,  how  do  you  
get  that  date?    Even  if  you  see  someone  who  checks  off  all  your  “boxes”  if  you  will,  
do  you  know  how  to  start  conversation  with  them?    Even  if  you  work  up  the  courage  
to  approach  them,  what  do  you  say?  
 
 
     
 

 
 
 
 
 
 
 
 
 
 
 
 
 
  9  
Chapter  3:    
 
Flirting  and  Approaching:  How  To  
 
The  “how”  of  trying  to  approach  and  flirt  can  be  so  intimidating,  that  a  lot  of  
potential  love  matches  go  unapproached.    Let’s  change  that  for  you.      
 
You  may  be  surprised  to  hear  that  most  people  are  flattered  when  approached.    
 
Even  if  you  know  what  you’re  looking  for  in  a  partner,  it’s  completely  normal  to  feel  
nervous  when  approaching  or  flirting  with  someone  you’re  interested  in.    
Approaching  is  like  an  art,  you  just  have  to  keep  practicing  over  and  over  again,  and  
eventually  one  will  bite.  

What  about  that  woman  you  see  every  day  in  the  line  at  Starbucks  on  your  way  to  
work?    Often  times,  you’re  standing  right  in  front  or  behind  her  in  line,  and  on  
occasion  have  exchanged  a  smile.      
 
The  smile  is  a  good  start.      
 
It’s  crucial  not  to  overthink  flirting  and  approaching  too  much.  Flirting  and  
approaching  is  not  as  complicated  as  some  would  think  and  a  lot  of  the  time  flirting  
happens  organically  when  you  like  someone.  With  that  in  mind,  that  initial  
encounter  with  someone  you  like  can  feel  scary!  

For  those  that  are  struggling  with  ways  to  flirt,  approach  and  start  conversation,  
here  are  8  strategies  to  get  that  introduction  on  your  way  to  a  first  date:  

1. Make  eye  contact:  That  initial  interaction  really  start’s  with  the  eyes.  See  
someone  you  like?  Make  eye  contact,  smile,  and  then  look  away.  No  creepy  
stares,  you  are  just  showing  them  you  noticed  them.  That  initial  eye  contact  
may  happen  a  few  times  before  either  of  you  strike  up  the  nerve  to  start  a  
conversation.  
2. Smile:  A  smile  is  one  of  your  biggest  assets.  Smile  at  the  person  you’re  
interested  in.  It’s  a  great  start.  
3. Introduce  yourself:  Not  sure  how  to  spark  up  conversation?  Sometimes  it’s  
as  simple  as  introducing  yourself  to  your  person  of  interest!  From  there  the  
conversation  may  just  flow.  
4. Compliment  them:  Another  way  to  start  conversation  with  your  person  of  
interest  is  to  give  them  a  sincere  compliment.  If  you  love  their  hair  or  you  
like  their  tie,  tell  them!  A  simple  compliment  shows  interest  and  helps  to  
keep  you  out  of  that  friend  zone.  

  10  
 5. Ask  open-­‐ended  questions:  When  you’re  flirting  and  have  the  conversation  
going,  ensure  to  ask  open-­‐ended  questions.  Answering  with  one-­‐word  
answers  will  not  get  you  far.  Try  phrases  that  include,  “Tell  me  about…”  You  
want  to  eliminate  the  yes  and  no  answers  as  much  as  possible.    When  
approaching  anyone  you  want  to  break  into  a  conversation  using  an  
observation  of  the  work  around  you.      
6. Friendly  touching:  When  you  really  like  someone,  part  of  flirting  is  getting  
close  to  him  or  her.  When  I  say  friendly  touching,  I  mean  a  light  graze  of  their  
arm  or  you  may  “accidently”  touch  feet  under  the  table.  Keep  any  touching  
respectful  and  not  too  forward.  
7. Tease  them:  Any  opportunities  to  tease  someone,  adds  a  light,  fun  vibe  to  
the  flirting.  Just  ensure  your  person  of  interest  knows  you’re  joking  when  you  
tease  them  and  do  not  let  the  teasing  brink  on  insulting  them.  
8. Don’t  over  stay:  Part  of  flirting  is  knowing  not  to  over  stay.  If  you  just  met  
this  person,  have  a  light  conversation  with  them,  then  excuse  yourself  and  
continue  on  with  your  night.  If  there  is  an  opportunity  there,  tell  them  you  
would  like  to  see  them  again  and  ask  them  for  their  number.  

There  are  many  ways  to  flirt  and  approach,  but  the  way  you  flirt  ultimately  comes  
down  to  your  own  comfort  level.  That  first  interaction  aside,  you  really  won’t  have  
to  over  think  the  ways  to  flirt  and  approach  when  you  start  interacting  with  
someone.  The  chemistry  with  the  right  person  will  move  you  forward.  

Here  are  some  other  things  to  keep  in  mind  when  you’re  approaching  your  potential  
date:  

ü Let  go  of  the  cheesy  pickup  lines,  they  are  overused  and  could  ruin  your  
chances  of  getting  a  date.    
ü Don't  be  afraid  to  take  risks,  no  pain  no  gain.    You  may  never  see  this  
person  again,  are  you  willing  to  take  that  chance?  
ü If  you’re  a  man  approaching  a  woman,  compliment  her  but  not  on  how  
beautiful  she,  (a  beautiful  woman  hears  this  all  the  time)  try  complimenting  
her  shoes,  accessories  or  hair!  

With  these  dating  approaches  and  techniques,  you’re  more  than  guaranteed  of  
getting  that  first  date  if  you  stay  persistent  on  your  quest  to  find  the  right  partner  
for  you.    Keep  approaching;  keep  putting  yourself  out  there  and  it  will  happen.    

 
  11  
Chapter  4:        
How  to  Ensure  You  Get  The  Second  
Date  
Now  you  have  a  first  date  scheduled,  you’re  already  starting  to  worry  about  the  end  
of  the  date  and  scoring  that  second  date!  

Your  ability  to  succeed  at  getting  that  second  date  starts  with  you  first  and  foremost.    
Use  this  10  point  first  date  makeover  to  ensure  you’re  first  date  ready.  
 
Single  in  the  City’s  First  Date  10  Point  Body  Makeover  Checklist:  
 
 
ü Hair:    How  does  your  hair  look?  Learn  how  to  style  your  hair  or  make  sure  to  
go  to  a  good  barber  or  hairdresser  that  can  help  you  with  some  good  styling  
tips  before  that  first  date.    Practice  makes  perfect!  
ü Eyebrows/nose  hair/ear  hair:    If  your  eyebrow  hairs  are  growing  out  of  
control,  they  need  to  be  trimmed.    Hair  should  not  protrude  from  your  ears  
and  nose  and  should  be  trimmed  regularly.  
ü Facial  Hair:    
o  If  you’re  going  to  have  a  beard  make  sure  it  looks  good  on  you  and  is  
well  kept  and  trimmed  regularly.    
o  If  you  do  have  a  beard,  make  sure  to  use  conditioner  on  it  to  keep  it  
soft.  
ü Lips:    Even  if  you’re  a  man,  keep  those  lips  soft.    Use  lip  balm  or  even  an  
exfoliator  on  your  lips!  
ü Skin:    Soften  that  skin  by  using  moisturizer.  
ü Smell:      
o Bathe  regularly,  use  deodorant  and  make  sure  to  choose  
cologne/perfume  that  suits  you  and  that  does  not  overwhelm  your  
date.      
o Chew  a  mint,  brush  your  teeth  and  floss;  make  sure  your  breath  
smells  good.  Carry  gum  or  mints  with  you.  
o Don’t  eat  garlic,  curry  or  onions  within  24hrs  before  a  date  
ü Shoes:    Make  sure  your  shoes  are  not  scuffed  and  are  free  of  dirt  and  
grime.    Men,  women  can’t  help  but  notice  and  evaluate  men  by  their  shoes.    If  
you  need  help  in  the  shoe  department,  ask  a  friend  or  personal  shopper  for  
help.    
ü Posture:    Always  sit  and  stand  up  straight,  not  only  does  it  look  better  but  it  
exudes  a  level  of  confidence.    Trouble  with  your  posture?    Try  practicing  yoga  
or  seeing  a  chiropractor.    

  12  
 ü Clothing:    Everyone  has  their  own  sense  of  style  to  some  degree,  but  for  
some,  you  may  not  be  as  confident  in  picking  out  clothes  and  styles  that  suit  
your  personality  and  body  type.    If  you’re  unsure  what  clothing  to  wear,  ask  a  
friend,  pick  up  a  magazine,  go  online,  or  better  yet,  hire  me  to  take  you  
shopping!      Women  in  particular,  love  men  that  have  a  sense  of  style.    General  
rule  of  thumb  when  it  comes  to  clothing  is  when  in  doubt,  don’t  wear  it.    
ü Teeth:    Make  sure  you  clean  your  teeth  regularly  to  get  rid  of  plaque  build-­‐up  
and  stains.    Floss  and  brush  your  teeth  regularly  
ü Makeup:    For  women,  make  sure  your  makeup  is  not  over  the  top.    Keep  it  as  
natural  as  possible,  while  still  accentuating  your  best  features.    You  want  to  
steer  away  from  makeup  that  causes  you  to  look  like  an  entirely  different  
person  to  your  date  each  time  you  see  them.    
 
 
How  to  Get  The  Second  Date    
 
Scoring  the  second  date  is  in  many  cases  a  lot  harder  then  sealing  that  first  date.    For  
a  second  date  to  be  on  the  radar,  you  have  to  ensure  you’re  yourself  and  put  your  
best  foot  forward.  
 
Many  people  go  on  first  date,  after  first  date  and  never  know  what  they’re  even  
doing  wrong.    It  could  be  something  as  small  as  your  cologne  is  overpowering  your  
dates,  you  have  a  nose  hair  out  of  place  or  you  tend  to  talk  about  your  ex’s  too  much.      
 
Single  in  the  City  has  put  together  a  checklist  for  you  to  review  before  going  on  that  
first  date.    Look  back  at  your  previous  dates;  are  you  guilty  of  any  of  these  first  date  
faux  pas?  
 
Be  real  with  yourself,  your  dating  success  is  dependent  on  your  ability  to  really  
check  in  with  yourself  and  make  changes  where  necessary.      
 
Below  are  20  Things  You  Should  Never  do  On  a  First  Date  

1. Show  up  late.  Showing  up  late  for  a  first  date  demonstrates  a  lack  of  regard  
for  the  other  person.  
2. Ignore  your  appearance/hygiene.  First  impressions  count.  You  don’t  need  
to  change  who  you  are,  but  it’s  important  to  present  the  best  possible  version  
of  you.  
3. Overload  the  cologne.  We  want  to  entice  our  date,  not  suffocate  them.  
4. Have  your  phone  out.  Texting  or  answering  calls  on  a  first  date  is  a  big  no-­‐
no.  Do  yourself  a  favour  and  keep  your  phone  in  your  pocket  or  your  purse.  
5. Talk  about  your  ex.  Talking  about  your  ex  on  a  first  date  is  a  huge  turn-­‐off.  If  
you  feel  the  urge  to  talk  about  your  ex,  perhaps  you  are  not  over  them  and  
should  not  be  on  a  first  date  to  begin  with.  
6. Interview  them.  Do  not  grill  your  date.  

  13  
 7. Poor  manners.  Poor  manners  such  as  swearing,  picking  your  teeth  or  licking  
your  fingers  are  not  a  good  first  impression.  
8. Go  over  the  top  planning.  First  dates  are  meant  to  be  relatively  casual.  You  
don’t  want  to  over  plan  for  a  first  date  and  make  your  date  feel  
uncomfortable.  Going  out  to  a  nice  restaurant  or  a  pub  is  a  perfect  way  to  get  
to  know  someone.  You  do  not  need  a  5-­‐star  restaurant  to  do  that.  
9. Plan  a  movie  date.  First  dates  are  meant  to  get  to  know  the  person;  you  
can’t  do  that  if  you’re  not  talking.  
10. Get  drunk.  Having  a  drunk,  sloppy,  slurring  date  is  not  attractive.  
11. Express  your  desire  to  have  children.  Use  the  first  date  to  see  if  you  have  
chemistry  and  compatibility  with  your  date  first  before  you  move  onto  the  
serious  relationship  discussions.  
12. It’s  great  to  think  you’re  great,  but  don’t  overdo  it  by  only  talking  about  
yourself.  Make  sure  you  are  expressing  interest  in  what  your  date  is  all  
about  too.  
13. Not  eat.  First  dates  can  be  nerve  racking  but  picking  at  your  food  is  only  
going  to  confuse  your  date  and  make  them  think  you  can’t  be  yourself  and  
are  uncomfortable.  
14. Be  negative.  Keep  the  date  positive.  
15. Start  talking  about  a  second  date  before  the  first  is  over.  Don’t  get  ahead  
of  yourself.  Be  in  the  moment  and  enjoy  the  first  date.  There  will  be  plenty  of  
time  for  planning  later  if  it  goes  well.  
16. Expectations  over  pay.  Never  expect  that  the  other  person  will  pay.  It  is  
gentlemanly  to  have  the  male  pay  on  a  first  date,  but  never  act  as  if  you  
expect  it.  
17. Check  out  other  people/flirt  with  people.      Focus  on  your  date.  
18. Make  sexual  references.  Diving  into  the  sex  talk  too  soon  can  give  your  date  
the  wrong  impression.  
19. Over  share/Revealing  family  history.  You  do  not  need  to  reveal  everything  
about  yourself  and  your  history  on  a  first  date.  
20. Don’t  be  creepy  postdate.  Resist  the  urge  to  immediately  add  your  date  to  
social  media  or  text  them  non-­‐stop.  Give  them  enough  space  to  process  the  
date;  at  least  a  day.  

Now  that  you  know  what  not  to  do  on  that  first  date,  let’s  recap  with  some  First  Date  
Reminders:  

ü Smell  nice  and  take  pride  in  your  appearance.    Ensure  you’re  well-­‐
groomed,  smell  good  and  dress  in  clean  clothes  (as  obvious  as  that  can  be  for  
some).  When  you  know  you  look  good,  you  feel  good  and  it  allows  you  to  
project  the  most  positive  version  of  yourself  for  your  date.  
ü Don't  be  overly  touchy.    Personal  space  is  important  as  you  get  to  know  
your  date.    It’s  important  to  pay  attention  to  the  queues  your  date  could  be  

  14  
 sending  your  way.    
ü Always  remember  to  smile.      
ü For  men,  chivalry  is  not  dead.    What  does  this  mean?  
• Hold  the  door  open  for  her.  
• If  you  are  picking  her  up,  open  the  car  door  for  her.    
• Pull  her  chair  out.  
• Pay  the  bill  without  being  obvious.    
• If  the  night  gets  cool,  offer  her  your  jacket.      
• If  you  are  doing  an  activity  and  she  needs  assistance,  
offer  a  hand.  
ü Prepare  questions  to  ask  and  be  as  good  of  a  listener  as  you  are  a  talker.      
Feel  free  to  tell  your  own  story  but  make  sure  your  date  is  an  equal  party  to  
the  conversation.  This  date  isn't  about  you  rattling  off  your  accomplishments,  
it's  about  engaging  with  a  new  person  and  seeing  if  you  connect.  
ü Express  your  interest  in  seeing  them  again  before  the  night  is  up.  A  
simple,  “I’d  love  to  talk  more  about  this  sometime”  or  “I’d  like  to  see  you  
again.”  And  if  you  mean  it,  always  end  the  date  with,  “I’ll  call  you.”  
ü Going  in  for  that  kiss.    What  is  your  dates  body  language  telling  you?    Are  
they  smiling  at  you?    If  the  date  is  going  well  and  your  date  is  flirting  with  you  
and  takes  those  opportunities  to  move  their  body  proximity  towards  you;  
these  are  all  signs  that  your  date  likely  wants  that  first  date  kiss.      When  in  
doubt  go  in  for  a  hug  first  or  ask  your  date  if  they  mind  if  you  give  them  a  
kiss.    When  done  properly,  asking  your  date  for  a  kiss  can  be  really  sweet!  
ü Don’t  be  creepy  postdate.  Resist  the  urge  to  immediately  add  your  date  to  
social  media  or  text  them  non-­‐stop.  Give  them  enough  space  to  process  the  
date;  at  least  a  day.  
 
I  truly  believe  that  incorporating  these  strategies  and  techniques  into  your  dating  
life  can  yield  immediate,  positive  results.    Remember,  practice  makes  perfect,  always  
follow  your  intuition  and  never  settle  for  any  relationship,  but  the  one  you  deserve.    
Long  lasting  love  relationships  are  out  there  and  that  second  date  is  attainable.    For  
the  right  person,  you’re  more  than  enough.    Rejection  can  be  a  blessing  in  disguise  
and  it  is  through  rejection  that  we  learn  most  about  ourselves  and  what  we’re  truly  
looking  for.    
 
The  person  of  your  dreams  is  out  there.    In  fact,  the  next  date  you  go  on,  could  be  the  
date  of  your  dreams  and  future  partner.    
 
Envision  it  and  believe  it,  it  will  happen.  Trust  that.    
 
 
 
 
 

  15  
LAURA  BILOTTA  
Laura  Bilotta  is  a  date  coach,  matchmaker  and  the  founder  of  successful  dating  
website  singleintheicity.ca.    Laura  established  Single  in  the  City  in  2002.    Since  its  
early  beginnings,  Laura’s  efforts  and  expertise  have  allowed  Single  in  the  City  to  
become  one  of  the  largest  event  based  dating  companies  in  the  Greater  Toronto  Area.    
 
Laura’s  expert  knowledge  of  dating  etiquette,  relationships,  and  human  behaviour  
form  the  base  of  her  experience.  She  has  hosted  over  one  thousand  speed  dating/mixer  
events,  coached  more  than  one  hundred  men  and  women  into  dating  gurus,  and  she  
has  proudly  played  matchmaker  for  countless  love-­‐seeking  singles.  
Laura  is  the  host  of  Dating  Talk  show,  Single  in  the  City  on  Rogers  Peel.  

 
 

  16