Lipstick on your teeth?

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Recently it has been on my mind, how do you tell a friend that they’ve lipstick on their teeth (or face)?  I’ve a lovely dear friend, she’s a great laugh but more than a tad nervous of herself.  She apologises a lot, worries that she doesn’t look right, or that there’s something amiss.  Her body shape has changed a lot since having two beautiful girls and I think this has knocked her confidence.  I didn’t know her before, but honestly, the woman has fabulous taste in clothes and I think she dresses wonderfully!


When it comes to makeup however, she needs a wee helping hand.  Like myself, she never really did makeup, or when she did, it was punk/goth heavy liner look.  Now she’s trying to get back into makeup, but not the old look and maybe not quite getting the hang of it.   She tends to end up with her lipstick on her teeth and then due to nervousness she’ll wipe her lip, then touch her face.  So it ends up on her cheek too.  
I’m not sure how I tell her that she’s done it, I don’t want her to become even more nervous and I don’t want to offend her.  She’s such a lovely gentle sweet person.  With some of my other friends that I’ve known for 10 years or more, well we can easily laugh about it!  In fact I have taken a friend in hand before going on a night out, wiped her face clean and reapplied her makeup!  So I’ve had a think about what to do and I’ve come up with a solution of sorts. 
She has a lovely night out coming up with her husband, so I’ve offered to go to her house and give her a mini makeover.  I’ve got some nails for her and as she’s very similar colouring to myself, I can use my products on her.  She’s delighted!  So I’m hoping that I can throw in some useful hints & tips along the way.  We’re also planning an evening at mine, to drink some wine, play with makeup and show her how to do various simple looks – I’m no expert but I’ve got the hang of the basics.  Plus we can round it off with some face masks!
Just in case, here are three things that help me
1. Fill your lips with lipliner before applying lipstick – especially with a lipstick that tends to move!
2. Blot between applications.
3. Suck your finger while pulling it from your mouth to help remove excess from the inner part of your lips.
That should help reduce the risk of lipstick on your teeth!  Have you had to deal with similar issues?  How have you helped?

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