Flirting Tips

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Some tips which attendees offered on flirting (aka "casual conversation with a romantic spark") were:

The topic of rejection came up. The key thing to understand about rejection seemed to be that "everybody gets rejected once in a while." A related idea was that if you never risk rejection it's likely your social life will end up being very dull. It was also mentioned that the range of tastes in body type and personality type is enormous; something that you think is a liability is for some people almost certainly a turn-on.

The question came up of how to tell if someone is interested in you. The following were mentioned as clues, especially when observed together:

There's a lot of crossover between good listening skills and good flirting skills.

One attendee shared some interesting ideas on the importance of "validating what the other person wants to be." This means looking for specific ways in which how someone thinks of themself as unique and valuable is consistent with their actual behavior and history.

Asking questions that are "almost too personal" was also brought up. The idea is that humans progress to greater levels of intimacy by sharing vulnerabilities, and that if someone is interested in you they are unlikely to turn down the chance to make the conversation more personal (unless you REALLY push the envelope, obviously...)

The importance of giving sincere complements was mentioned more than once.

Social networks usually expand by cultivating friendships which are serious enough for your new friends to introduce you to their friends. For this reason, activities that allow prolonged contact with other people are valuable.


By way of comparison, the following is a sampling of the ideas presented in a typical mainstream book about flirting.

Here are Ms. Jillson's three biggest tips on flirting:

  1. Be friendly.
  2. Don't let past rejections cloud your judgement or make you paranoid about an interaction going on right now (that's fair to neither of you).
  3. Be prepared, both physically and emotionally. This means looking your best as often as you can (people do meet in the oddest places...), and not dragging past or present personal troubles into a new interaction.
Here are Ms. Jillson's tips for "being popular":

Other ideas she mentioned included "being playful yet persistent," showing vulnerabilities, flirting with no expectation of reward (i.e. just for fun, without a win/lose mentality), learning to dance, and contributing and/or appreciating good humor.

Ms. Jillson's "Ways to be a Great Flirt":

  1. Use flattery
  2. Say "Hello" with energy
  3. Shake hands (depending on circumstances)
  4. Make immediate, direct eye contact
  5. Repeat the person's name
  6. Ask "no one ever asked me that before!" questions
  7. Ask for your new friend's life story
  8. Whisper
  9. "Help someone get out of an old routine, and into a new one" (i.e. introduce them to some new activity or form of art or whatever)
Ms. Jillson's "5 Don'ts of Flirting":

  1. Don't depend on others to make things happen
  2. Don't tease (i.e. offering more than you intend to give)
  3. Don't cling
  4. Don't dwell on your performance
  5. Don't fidget

Appropriate use of touch was discussed at length (psychological studies show that casual touching during a friendly conversation causes people to remember the conversation more fondly after the fact). Ms. Jillson mentioned brushing lint off someone's jacket, touching someone's hand as punctuation to making a point in the conversation, etc. "Accidental touch" (i.e. reaching for the saltshaker at the same time) was also mentioned favorably.

Here's what Ms. Jillson has to say about eye contact: "While staring or holding a gaze a second longer than usual will succeed in attracting notice, so will other subtle and more tasteful eye contact; try this: Throw a glance to a person, and then, as soon as your flirting partner turns to meet your gaze, immediately lower your eyes. This is very effective for both men and women."

At cocktail parties and such, often one of the hosts will introduce new people to other people at the party. When being introduced, Ms. Jillson's advice is to "always put out your hand and always say the person's name and always ask a question." The conversation needs to get started somehow, and unless something more substantial appears than the handshake the introduction is just going to sit there. If you forget someone's name, take this as an opportunity to talk to them again just before you leave.

Ms. Jillson strongly discourages the use of "pick up lines" or other pet phrases to start conversations; they almost never seem to come off well. Also, questions which have "yes/no" answers tend not to be the best conversation openers; questions which begin with "I feel," "I think," "I wonder," etc. are better.

Ms. Jillson's tips for flirting at parties are:

  1. When you first get there, grab some food or a drink and notice what seems to be going on socially, what the dynamic seems to be, etc. The people who seem lost will be the easiest folk to successfully flirt with.
  2. Assume that everyone is socially nervous; cut them some slack if things initially seem awkward, and look for ways you can make people more comfortable.
Ms. Jillson's tips for creating a flirtatious and cozy environment at home are:

  1. Have a cozy place to sit (those L-shaped couches are best).
  2. Keep the temperature on the warm side.
  3. Be able to adjust the lighting (dimmer switches are nice, and candles are probably the most romantic way to illuminate the room).
  4. Clear out your medicine cabinet: keeping old bottles of prescription medications for maladies you no longer have invites idle (and often incorrect) speculation.

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