Should I Be Facebook Friends With A Guy Before He Is My Boyfriend?

woman lying on bed while responding emails using her laptop
A few years ago, after I broke up the love of my life, I had a really hard time removing him from my life, but the online part stung the most. I can throw an object away pretty easily, but de-friending and deleting someone from my entire online life – Facebook, Flickr, LinkedIn, not to mention hundreds of saved emails and dozens of sweet and funny text messages – hurt so much because it was almost like I had to relive our entire relationship over again or face the possibility of a status alert or old email catching me off-guard. It sucked and I never wanted to have to do that again.

After that, I decided that I will never be Facebook friends with someone I’m dating…at least until after we’re in a committed, exclusive relationship. I also won’t follow them on Twitter. And I also delete every email as I receive it (after responding to the message, of course!), and that’s the primary reason for my question. I don’t know if this is a good idea or if I’m just setting myself up for failure by being such a pessimist…because I’m deleting the messages NOW so that I won’t have to delete them LATER (i.e., after we inevitably STOP seeing each other). Is deleting them a bad thing (because it seems to be guided by fear) or is keeping them a bad thing (because doing so would be guided by the blinding fun/excitement/emotions of the possibility of a new relationship?) —Valerie

Dear Valerie,

If my wife thinks that spending 90 minutes doing her hair and makeup is an efficient use of her time, should YOU spend 90 minutes doing your hair and makeup?

If your best friend thinks that “occasional” drug use is harmless and doesn’t impact other areas of his life, should YOU start doing drugs?

No and no.

That doesn’t mean that what you’re doing is healthy, but you already knew that.

So if I, a 38-year-old married dating coach, with a penchant for logic, a nostalgic streak, and a high tolerance for emotional upheaval, tells you that you’re being silly by deleting everything any man ever writes to you, are you actually being silly?

Of course not.

That doesn’t mean that what you’re doing is healthy, but you already knew that.

You’re firmly established as a “pain-avoider” instead of a “pleasure-seeker”.

Pain-avoiders live their lives in fear. They won’t go online because men are players. They won’t get set-up because it never works. They won’t hook up with a guy because he may not want to commit. They try to figure out whether he’s a husband after three dates and pull away if they see any hint of a red flag. As a result, pain-avoiders are VERY successful at avoiding pain; they’re just TERRIBLE at finding love. Their whole existence is structured at protecting them from being emotionally vulnerable.

I’m the complete opposite of you, Valerie.

Pain-avoiders are VERY successful at avoiding pain; they’re just TERRIBLE at finding love.

I have every email that’s ever been written to me by a random woman from JDate. I have photographs of every girlfriend I’ve had in 15 years in Los Angeles. I am friends on Facebook with, um, too many people that I’ve seen naked. (The only ones I’m not friends with are women like you, who have deleted me because it’s too painful. Really? 9 years later?)

So while I understand that YOU think that digital communication means reliving your past; for me, it means not forgetting my past — no matter how painful it might have been.

Now is there any real benefit to saving all of those emails, those photos, those exes? Not really. I’ll admit, I’m a bit of a “hoarder” when it comes to sentimental stuff — that’s the writer part of me. But it seems a bit extreme to purge yourself of all traces of a potential husband WHILE he’s still courting you.

I mean, it’s not like there’s a tangible downside to cleaning out your inbox and separating your men from your friends the way others separate their personal and business expenses.

To me, it’s more symbolic. You’re bracing yourself for failure. And although I can say that 99% of all men are NOT your future husband and that failure is the default setting in any relationship, do you actually want to be a pain-avoider? Or do you want to be a pleasure seeker? Which one do you think is happier? More attractive to the opposite sex? More open and vulnerable and willing to take a chance on love?

Once you know the answer, the rest will be self-explanatory.

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  1. 1


    Like you, I keep the emails from my old boyfriends and potential boyfriends. I have had the sweetest email exchanges with great guys who waxed poetic, men with whom I shared silliness (they still make me smile). Whenever the dating pool is low, I can always reread these emails and remember the hope and thoughts of possibility at the start of those relationships.  

    The fact that they didn’t continue is just part of the journey. I learned so much from each guy I dated. They helped me figure out who to date next.

    My ex-husband was very jealous of my old boyfriends, and in a fit of rage at the beginning of our marriage, he went through old photos and ripped them up. I was furious. I wish I had those photos today. Not because I have regrets or want to seek those guys out, but because the memories were sweet.

    I liked what you said about pain avoiders and pleasure seekers, and couldn’t agree with you more.


  2. 2

    I can understand why Valerie would want to avoid pain, I’ve done the same thing, but in the end it still hurt or maybe still does, no matter what you do with old pictures or emails and such.   I still see my ex-wife on a regular basis because we had a child together and now we share custody.   So, no matter what I did with all of the emails, texts, and photos of our life together, I still will be reminded of the pain of our split.
    But you know what?   I’m glad I haven’t deleted those memories.   There was a time when things were good and I don’t want to throw that part of my life away.   I don’t want to forget that there was a time when I was in love and loved back.   How could those be anything but good memories.
    Like Sandy said, you learned something from that relationship and can take that with you on the rest of your journey.   To ignore it would be a shame.

  3. 3

    Great Article on facebook dating.

  4. 4

    I collect, I never delete but I almost never look at emails, sms etc I have collected.

    Why would I want to remember something from the past, when it is gone?

    I seem to forget people, things, occations, especially sex.. everything that happened yesterday, is almost out of my memory.
    I have learned to dislike people that remind me how things that were, when the time for that has gone… I don’t want to drag unnecessary thoughts or memories around – Not that it is painful really, but because they are past, and why would I want to live in the past, when I want something better for the future.

    Hmmm…. I guess the amnesia started when my ex once said after sex that “you will always remember this time” – when that intercourse was nothing to brag about, in fact it had been “same old” as usual, meaning that he got his O, and I was left wanting”.. (I settled from sexual attraction when I entered to that relationship, and I paid for it…   I remember nothing of sex with him.. other than it was boring most of the time when he refused to listen what I liked even if I showed him and returned to do what he thought I wanted..) but words that he said left an impression that came up as I thought to write this. =/
    Well, things past, why relive them second time? Booooring

    I don’t cut men out really afterwards.
    When I lost the interest, they are just friends, and as such I may/can talk with them regularly.. but they often don’t get the fact, that when I’ve lost interest, then I am just not interested in hearing references to sex even if they still see me sexually.
    When relationship is over I am off to newer pastures and fresher males that are there, and I am sure the ex sexpartner doesn’t want to hear of that either.. anymore than I want to hear vealed references to what happened between us before on his kitchen table. (I notice them from the pregnant pause or knowing look, and then I know that man in question was refering to something that should ring a bell)

  5. 5

    Maybe you just aren’t ready for a new relationship.

    Hopefully, you will come full circle, realize mistakes from your previous relationship on both your and his end, and can get to a point where you realize the good moments outweighed the pain of the breakup and want that again.

    Healing takes time.   I don’t think it’s bad that you are still in “pain-avoider” mode.   Just will yourself to heal and get out of it.

    Do I think your current ideas about relationships are healthy?   I agree with Evan – no.   I don’t want to start friending someone on facebook or following them on twitter the minute I meet them.   It’s just an over-access to information that is better to learn b/c the person tells you anyway.

    Wouldn’t you rather find out about their siblings or their job or their recent vacation because they told you about it, not because you looked it up?   Waiting until you are committed is ok.   But I think deleting emails is where you are crossing a line.   There is no reason to delete these emails.   

    I believe it is in your best interest to work to get to the point where you WANT these emails to be your life.   You should want these to be your new memories.

    Can you remember how happy originally receiving those messages were from your now ex?   So focus on the happiness, not the pain.   Attempt to recreate that level of happiness.

  6. 6

    I just don’t see what the big deal here  is  at all. Maybe I’m not very sentimental, but there is no way I would want to save hundreds of emails, dozens of text messages from anyone, much less someone I may have dated short term if that’s the way it turned out. I don’t see Valerie as a “pain avoider” particularly, I see her as a woman who thinks pragmatically.   If a relationship grows and continues, she will have the guy – she doesn’t need every early communication he ever wrote. And should a dating relationship prove brief? Who needs to come across reminders of something that went nowhere? The idea of connecting with someone  in social network  after connecting with them exclusively in person makes perfect sense to me.

  7. 7

    Evan, I had to chuckle at this: “I’ll admit, I’m a bit of a “hoarder” when it comes to sentimental stuff — that’s the writer part of me.” This is exactly the reason why I save personal emails from men. I like to write, and hope to be published someday. These emails are writer’s gold. As an added bonus, there’s even poetry in there!
    Facebook, though, is IMO a completely different beast. With our families, close friends, business relations, and coworkers on our friend lists, we’ve got to be careful about who we add. As for the guys I’ve dated, I added two of them. One left me a PA message on his wall (not on mine, thankfully). The other one made a dirty reference to me in a Facebook conversation with his siblings that was up on his wall for all his friends to see. The first one deleted me; I deleted the second one. Next time, I’ll probably move in together with a guy before I add him to my Facebook.
    So my advice to the LW is, nix the social media, but feel free to save the mementoes!

  8. 8

    For me, these are different issues. I had an LDR with a guy where we exchanged lots of fun and informational emails. I liked him a lot at the time and haven’t had the heart to delete his messages, mainly because they contained links to lots of interesting things.  

    But I wouldn’t Facebook-friend a guy I’m just getting to know, because I don’t like having to “unfriend” someone or be unfriended myself. I exclusively dated a guy who would check to see if I was on Facebook, and want to spend half the day IMing there. I had to hide my online status! Later, I found out he wanted to break up when he simply un-friended me without any sort of actual conversation – nice, right?

    I think I am part pleasure-seeker and part pain-avoider!  Sandy #2, has a great attitude (definite pleasure-seeker), by the way.  

  9. 9

    It’s interesting that she is anticipating being hurt.   Could it possible end because she wanted it to and there be no pain on her end?     Hmmm   Sounds to much like a victim for my taste.       Maybe some building up is needed before you date again.

  10. 10

    I unfriended my ex after a really painful breakup– the updates and new pictures would just be a reminder that I wasn’t part of his life anymore.   But six months later, I’m happy i didn’t delete all our emails because, as other posters said, it’s nice to be reminded that I found someone once and will find someone again.   And certainly while you’re falling for someone, it’s nice to hold onto those reminders that he’s thinking of you.
    Like Evan said, there’s nothing really wrong with deleting those correspondences, if you want to.   But probably the real issue is realizing that if you break up, you’ll be okay.   Deleting them now won’t make a breakup easier, but fearing a breakup will make getting into the relationship harder.   If you do break up, you can figure out what to do with all the written records of the relationship if they make your life harder.   Most importantly, enjoy your relationship now and believe you’ll be able to move ahead if it doesn’t work out.

  11. 11

    I think it’s perfectly understandable to delete e-mails, old photos, social-media links with exes. Some people are cool with everyone they’ve ever dated being their Facebook friend, especially if you use Facebook as a promotional tool more than a place for your closest pals. But some people have a tough time seeing their exes succeed (or simply move on) via Facebook or Gchat status.

    I tend to save correspondence and mementos, but whenever I’ve tossed things out, it’s been for the better. My entire old Yahoo account was deleted somehow (I blame Yahoo), and all of my e-mails from my college ex were deleted. It was a bummer, but it left me lighter – because along with the gushy letters, I also had old e-mails from him when we were fighting that weren’t so nice. Same with my most recent ex: He de-friended me on Facebook, and I am so glad. I had already taken him out of my newsfeed, but it was still tough to see him with his new life, even though I had no desire to get back together with him. I’m glad he took himself out of the equation.

    I think it’s a case-by-case basis. I’m still friends with that college ex on Facebook, and I enjoy seeing what he’s up to now. Probably because I don’t harbor any ill will toward him!

    I say do what you feel comfortable with. No need to expose yourself to digital discomfort if you can avoid it. Go ahead and wait until you’re exclusive to friend a guy on Facebook. Doing so early on isn’t necessary to find a happy relationship.

  12. 12

    Valerie, I think deleting all of the old emails, chat  and SMS messages was necessary for healing, but that someday you may want to read them again, when enough time has passed and the pain is not so great.   I know that happened to me … I deleted hundreds of emails and chat messages from my ex when I found that all I was doing was rereading them over and over and crying inconsolably.   And perhaps that was OK to do … even though I thought it was prolonging my recovery.   I wish now I had just archived them.   I think someday when I am old I may want to go back and reread them, for nostalgia’s sake.   I rarely delete anything from anyone else though.   I guess it wasn’t as painful,or I didn’t have the same intensity of feeling about them.   Incidentally, my ex is the only person I have ever de-friended on Facebook … it was too painful to see the updates and comments left by his new girlfriend.   I don’t have a problem friending new boyfriends, but I wait now until we are in a relationship.   If it ends, I don’t de-friend them, and they don’t de-friend me.   On another note, I still have the love letters that my grandfather sent my grandmother when they were courting, and they are among my most treasured belongings.   Somehow, I don’t think emails will achieve that exalted status …  

  13. 13

    Valerie, you can friend him or not friend him.   What I mean by that is, there are people you have on Facebook that are close friends, others that are acquaintenaces, and others that are on your friends list that you don’t know from Adam and likely won’t interact with.   If you really want to add the ex bf, but are concerned that seeing his posts will bother you, then hide his posts.   Then they won’t be in your news feed.   It doesn’t make you a bad person either way.   I just started chatting with a guy that I feel ok with having as a friend on Facebook.   I’ve had others that I didn’t add because I felt like it would be too tempting to “check up” on them.   That’s the rule of thumb I use.   Do what is comfortable for you.

  14. 14

    Hi Evan! I love your response to her. I’m sure she knows what’s right and what’s not for her. Another great one from you! Thanks.

  15. 15
    BeenThruThe Wars

    There is a lot to be said for not “letting it all hang out” with a man until you are in a committed relationship.   Keeping a slight air of mystery — of a piece of your life that’s only accessible to your closest circle of intimates — is a good thing in the earlier stages of dating.   Heck, it’s a good thing when you’re married.   I would advise keeping your social networking pages a slightly more exclusive space, and not friending everyone who auditions for the role of boyfriend.   Once you are exclusive, then it’s kind of a nice thing to welcome each other into that next circle.

  16. 16


    I’m deleting the messages NOW so that I won’t have to delete them LATER (i.e., after we inevitably STOP seeing each other). Is deleting them a bad thing (because it seems to be guided by fear)

    I believe when we choose any action because we’re being guided by fear – It’s a bad idea.

    Your fear of a perceived future break-up has you in break-up mode right now!

    When you do fall in love you may wish you had those early emails, texts, cards to look back on and regret you were so hasty and trashed everything.

  17. 17

    Email can sit in a folder where you never have to look at them unless you choose to.       Friending someone on FB and becoming “friends” with their Facebook “friends” keeps pushing reminders of that person in your face long after the relationship is done with.
    “Friending” someone on FB soon after they are introduced into your life is not a good idea for other reasons.     You don’t know what they are like as people, what information about you or your real friends they will see or what they will do with that information if things don’t work out happily.
    Keep them off of your Facebook page until they are a BF and don’t be too fast to delete email.

  18. 18
    Karl R

    Valerie said: (original post)
    “de-friending and deleting someone from my entire online life — Facebook, Flickr, LinkedIn, not to mention hundreds of saved emails and dozens of sweet and funny text messages — hurt so much because it was almost like I had to relive our entire relationship over again  […] It sucked and I never wanted to have to do that again.”

    If you want to avoid feeling that pain again, stop having relationships.

    If a relationship ends, there’s going to be pain. The more significant the relationship, the greater the pain. If a relationship doesn’t end, there’s also going to be pain … because getting along with someone over the long run can be a difficult and painful process. And the more significant the relationship, the greater the pain.

    Do you want a significant relationship badly enough to risk feeling pain?

  19. 19

    Personally, I don’t think that you should make someone your facebook friend, follow on twitter etc until you are in a committed relationship because then at least you are more sure of your relationship than you are at the dating stage. Although if things do not work out, there is still the pain of de-friending them, which I believe you should do in order to have a clean break and get over someone. Otherwise the temptation to peek into their life and pine will always be there.

    Also, this may or may not work for you, but you can create folders for text messages and emails where you may want to save communications and if things do not work out then all you have to do is click delete and it is easily sorted out in minutes, rather than trailing through your inbox. From personal experience, in the past I used to keep hold of old communications and would struggle to delete them and then a friend asked me why? Having given it some real thought I guess it was my way of holding on to the relationship that no longer was. Now I just go to my folders and click the delete button… despite how painful it may be.

  20. 20

    Good post, Evan. 🙂 I don’t see what else there is to say. Living in fear is not healthy. I can see deleting everything after, but before? This behavior seems kind of neurotic. Whatever the case, I think the men will pick up on the anxiety and take it as insecurity which normal men don’t find attractive.

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