Archive for the ‘ mailbag ’ Category

Dear Joey:

When do you think is the best time to give a potential boyfriend bad news?

Say you have to tell him you’re bipolar, or that you have an STD, that you’re on parole, or that you’ve have gender reassignment surgery. (Or something!)

Do you tell him before he gets to know you so that if he rejects you it doesn’t hurt as much and you didn’t waste as much time?

Or do you wait until you guys know each other better and then he may like you more and be less likely to reject you based on only a single piece of information?

I mean, for 2 of those scenarios, obviously you need to tell them before you have sex, but in general, is there a point at which it’s either too soon and not soon enough?

Potential Girlfriend

Dear Potential:

Great question!

Before I get in to what my thoughts are (your miles may vary) – I want to first point out that you have two different sets of information detailed here: things you’ve done, and things you are.

Things you’ve done that may be affecting you now are potentially bad news that may reflect negatively against you. In your examples, I would put the parole part right up there. The STD might fall there as well, depending on how you contracted it.

Things you are would definitely include being bipolar and being transgender. For the record, I would not count either of these as “bad news” – just facts. You are who you are are.

But I understand this is Earth, not Utopia, and people may react differently to you once they know these things. So instead of “bad news” – I think we need to discuss these as potential dealbreakers.

That being said, I wish there was a mathematical formula I could give on when the right time is to talk about stuff that could be troublesome, but there currently just isn’t. (I’m sure someone is trying to work on the algorithm, but for now we are just going to have to muddle through this.)

The Golden Rule of “do unto others” comes to mind. When would you want someone to tell you?

I tend to like the 3 date rule as a general baseline. Typically, the third date is symbolic for when you get more intimate with someone. The first date you are nervous and just trying to see if you get along. The second date you are checking out if this potential chemistry is a fluke, or if the lack of chemistry was due to nerves. By the third date, you are starting to see that this is going somewhere, but instead of just making this a physical mile-marker, make it a true intimacy moment and talk about who you are beyond liking baseball and thinking Kirk is better than Picard (or vice versa).

Things like the STD has a medical impact on your potential partner – you need to discuss it before sex, like you said. And if you are pre-op Transgender, that might be a bit of a surprise if you don’t discuss it before the clothes come off.

Any medical condition: being bipolar, having cancer, being allergic to bees – these are things you need to discuss if you are going to be in position where people around you may have to react. If you are going to spend the night or the weekend with someone, they need to understand that you have medication that you have to take, that you have appointments you have to go to, that you have an epi pen in purse.

But in reality, timing is something you have to figure out for yourself. What impact will revealing these things about you have on your ability to date? Is not telling someone going to prevent you from being yourself on a date because you are afraid of rejection? Then go ahead and get it out of the way – it may seem “too soon” to other people, but you are not other people – and you have to do what’s best for you. If someone will run after hearing that, it gets it out of the way.

As for other bad stuff in your past, like having gone through bankruptcy, or being a former nun or drug addict – I say, take that as it affects the relationship. This might not need to come up by the third date, but it definitely needs to be addressed before the 90 day rule – especially if the relationship has gone past casual dating to something potentially long term.

Again, just think about when you would want someone to tell you those things and use your best judgment. And remember that who you are is never bad news –it just might not be the right fit for someone unworthy of you.

Wishing you love and happiness –


Do you agree with me? Give your opinion in the comments section. Have a question? Send it to

Dear Joey,

I have been in love with a friend of mine for two years now and I hate it. If Friendzone was on Yelp, I would be the Duke of it. Any relationship I try to have to help me overcome this only works for so long before failing (as relationships do) and I know it’s not fair to them. I would do the whole “distance oneself from the problem” but we are both part of a core social circle and I don’t want to lose all of them too because of something I can’t get over.

Although my feelings have never been spoken outright, it’s probably as obvious as a tattoo on my forehead that I have feelings for them. However, I honestly have no idea. They are also single, have been for a while, and I think if there had been any interest, a move on their part would have already been made. I just wish I could make my feelings go away. It would be so much easier.

Help me, obi-wan Ke-Joey.


Arms tired from carrying this damn torch

Dear Arms Tired,

Being in a one-sided love crush sucks. Literally. It will suck the joy and hope right out of your life. Every interaction gets analyzed for hidden meanings and glimmers of possibility. Every goodbye makes you miserable again. Surely they must know, right?

Maybe. But maybe not.

I talked a little about this in Whoosh Factor, but what may seem obvious to you may be totally unnoticed by someone else.  I’ve had guys tell me that they asked me out or hit on me, and I really had no idea.  Even when I feel like someone is flirting with me, I’ll often talk myself out of believing it – it’s easier to justify that they are talking that way because I’m the organizer of the function we are at, or that they know that I’m a natural flippant flirt, or some other reason.

If you have watched the web series “The Guild” by Felicia Day- there is an example of this in the very first season.  To online gamer Zaboo, his love for fellow guildmate Codex should have been obvious.  He gave her game gold, they exchanged winking smiley faces, he crafted for her and helped her level.  She should know they were in a relationship, and so therefore, not be surprised when he showed up to her home and planned to move in. She, however, had no idea.

In your case, you admit, you have carried this torch for 2 years – so now what?  Well, put down the torch, and throw down the gauntlet too.  You have to tell them – just to make sure they know.  They may not have made a move because they have been just as scared as you, and thought you would make some sort of move showing you were open.  Or they could be just oblivious. Stop guessing and just put it out there.

I did this recently – and even though the guy and I never went on a date – it at least purged it out of my system.  Once I faced my fear and just asked him out, and got his answer, the torture was over.

It can be as simple as an email.  That’s what I did.  I just sent him an email and said – “Hey – I just want you to know – I think you are cute as heck and would love to go have a drink sometime.  If you are not interested, that’s cool – no harm, no foul.  But I figured if I never asked – I’d never know.”

He originally said yes, then he cancelled due to work and didn’t offer to reschedule.  Fair enough – point taken.  I saw him again at the next group thing, we gave each other hugs, and just acted normal.  You have to fake it at first – but then you know.  And that makes it easier.

Don’t worry about your friends.  They don’t even have to know.  As long as you remain chill, and your object of affection remains chill, and operate “business as normal” if it is not a match, then things will go on as normal, or transition back to normal.  No true friend is going to fault you for making your feelings known.  And any friend that does, as long as you don’t go all Sting “Every Breath You Take” stalker mode, is not a friend worth having.

The group will survive.  Don’t let the group keep you from pursuing happiness.  If I was being honest, anytime I’ve used my friends or my position as a reason for not making a move, the real reason was just that I was (bawk bawk bawk) chicken.   Because holding the torch was better than being empty-handed. Not having someone to pine over, for me, meant that I would have to start again in my quest for love.  That can be daunting, can’t it?

I’m proud of you for recognizing that carrying the torch isn’t healthy.  That shows you are strong enough to find out the truth and move forward with whatever result you get.  Please let me know the outcome – I’m happy to be your sounding board along the way.  Us love questers have to stick together!

Wishing you love and happiness –



Dear Joey,
My girlfriend has a male friend whom she has known a month longer than me. He lives [in another state] and has severe depression. He goes through these phases where he will get “needy” and constantly text or call her. I have expressed my dislike of this, since she really cannot be expected to devote all her time to him. A month ago he wouldn’t let her sleep with his constant calls. She feels that she is the only one who can help him through his suicidal thoughts. Before she met me she would cyber with him because he “needed” it. Now she won’t because she is with me in a relationship. He has starting asking for her to do that again and he has expressed a desire to have sex with her. She has pulled back some from him, not answering his texts as quickly and brushing off calling him unless he is really depressed. It is obvious I do not like the time she spends with him.

Here is the problem: she wants to go meet this guy. I am fearful what could happen. I don’t think she would integrally cheat on me, but with her depression, her mood swings and [other stuff] I don’t know what she might do. How should I feel about this?

What should I say?

Fearful Fella

Dear Fearful,

You owe it to yourself to be in a healthy relationship. You cannot forbid her not to be with this guy and the more he pushes her and she responds, the less healthy it is.

If she wants to go see this guy, she knows where it will go. This guy is an obvious user and that appeals to her somehow. You need to walk away until she figures this out. You don’t need to be the guy she’s physically closer to, but emotionally farther away from. Nobody wins that way.

(Before you walk away though, strongly suggest that this guy seek counseling and local help for his suicidal thoughts and depression. There are lots of free services out there he should be turning to, not to a girl who lives several states away. )

Please know that I think this guy is totally manipulating her. But distancing herself from him has to be her decision or else you are just going to end up with her resenting you or hiding it from you.

Of course, you may not listen to this advice because you may like broken, needy girls. Perhaps this is because you feel broken yourself. Do yourself a favor and become healed and healthy first – and look for others who are working on being healed and healthy too.

Wishing you love!

Do you agree with me? Give your opinion in the comments section.