Claire asked an interesting question on my You’ve Got Mail post. She asked, “It always seems so easy to be sassy and flirty on line but the thought of translating it all into real life is mighty scary. any tips on making the transition easier - and safer?”

Keeping it Real

Online dating can be a B~, particularly if you haven’t been keepin’ it real. But the fact is, if you live online most of the time, you will have to start being real some time with the people you interact with regularly. Consistency is a delicate thing over the internet, and the basis of a person’s credibility.

Point: If you are flirty and sassy online with someone, but you KNOW that you aren’t really as flirty/sassy offline… and you don’t intend to ever meet up with that person… you are fairly safe. But as friendships go, you will feel the urge to meet up with a chat mate in the future and be friends for real. Face-to-face real.

What you can do to make the online-offline transition smoother

• Come up with a disclaimer before your meet up - A line like “I may talk like this online, but off chat, I’m really a shy person” may get you far in terms of being ’safe’ on your first date.
• Do focus on your personality, not on your looks - A general idea of how you look is enough, and most people send each other photos anyway. It’s better to say “I laugh a lot” or “I love cheesy jokes” than “You know Jennifer Aniston? Well, she looks like me.”

Rule of thumb when discussing The Physical: Downplay your assets and the other person will discover them faster. If you’ve been highlighting your assets from the start, he will unconciously be looking for flaws. Much like a book story will always be more vivid than its movie version, a person’s mental image will always be more grand than reality.

Checklist Before the Offline Meetup

1. Review past chats and take note of the promises that you gave in the past (while you were being flirty and sassy) and decide whether to pretend not to remember them or ignore the fact that he wants you to remember them. Or, own up to the promises and keep ‘em.

2. Choose a descriptive outfit. Describing your outfit accurately is a lot better than asking your friend to look for the “long haired girl with a Venti Frapuccino”

3. Emotions check. Could you already be in love with this person? Are you expecting too much from this meet up? Be honest with your feelings before they run amok during your date.

After the First Real Date…

Scenario One: You still chat but less frequently (compared to the previous year of daily conversation), and mostly just hi and hello. The date could have been the first and last, and it’s time to move on. If you followed number 3 above and did a reality check on your feelings, you should be ok with the fact that maybe the other person didn’t share whatever feelings you might have been keeping.

Scenario Two: He insists on phone calls rather than chat, he sends emails rather than wait for you to show up on chat, he sends flowers and gifts on your birthday. Voila! That’s it… he’s into you for real. The only question is… are you into him too?