Lisa,

I have a rather unique problem that probably won't have an easy, happy solution but any insight would be appreciated.

A good (female) friend corresponds regularly by email with a man she met on a dating site.  This has been going on for about 8-10 months.  He has visited her a few times and she brought him over to meet me.  He seemed okay and she really likes him a lot.  She frequently says she believes this relationship is going to become a permanent one, etc.

Several weeks ago her computer went on the fritz and she doesn't have the money right now to get it fixed (waiting for her tax refund) so she asked if she could use mine to keep in touch with him.  I saw no problem with that so I said ok.  She stops by each evening to read his daily email and to reply.  She doesn't hang around or make a nuisance of herself.

The disturbing issue?  He has been sending emails to me saying he's really attracted to me and asking if there's any chance for something to develop between us.  I've not responded to any of his messages - I delete them so she won't accidentally see them.  I don't know if I should save the emails for her to read or just tell her what's going on or what.  I have not responded because I don't want to give him any ammunition and I know how emails can be tampered with so he has nothing from me.  She had given him my email address a while back and told him if her email wasn't working, he could contact her through me.  That was the only reason he has my address. 

She's a good friend who I like and respect very much.  I value her friendship and I worry how this knowledge would affect her.  Any words of wisdom about how to handle this?

Stuck in the Middle,
Kansas City, MO

Dear Stuck,

The solution to this problem is quite like the band-aid analogy.  You basically only have one option: you need to just grit your teeth and rip away.

Firstly, you’re right – there’s no need to respond to this “gentleman”.  However, I do think you should print out the emails he sent you, just to be safe.

Approach your friend the next night she comes to your house to check her email.  Have a pint of ice cream (and maybe a bottle of wine), at the ready.  Tell her about the emails he’s been sending you.  While you’re a good friend to be concerned about how this news will affect her, it’s only a matter of her finding out now, or later.  If he’s writing you emails, he’s surely writing emails to other women too – and there’s a good chance that if he’s not cheating on her now, he will at some point.  It sounds as if this relationship is somewhat long distance since they have been seeing each other for almost a year, but their primary contact remains to be over email.  This gives him even more opportunity to be unfaithful to her.

Help her get away from this guy as soon as possible.  It’s always easier to get through a break-up that ends sooner rather than later.  The longer she’s with him, the more upsetting the break-up will be.  And don't worry, she'll recover in due time.  And your friendship will be fine, too - once she accepts that this guy is the pits!

As for the printed emails, keep them aside just in case she doesn’t believe you, or requests to see them.  Don’t offer them up, because that may upset her even more – especially on the night you give her the bad news.

Best of luck!

Lisa

Gimme some more questions, at: lisa@relationshipper.com!