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Bonny Albo

Can I Date My Best Friend's Girl?

By July 30, 2012

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A gent who asked me to refer to him as "stricken" has written in asking for some advice about how he can turn a platonic relationship with his best friend's, friends with benefits into a dating relationship for himself. Or in other words, he's looking to ask out the woman who his best friend has been intimate with for the past year.

Stricken says: "My best friend for many years has a friend with benefits he has been seeing for a little under a year now. He met her through a mutual friend and they drunkenly hooked up one night and continued the trend to this day. From the day I met this girl I have been crazy about her. Seeing her has been few and far between but when I do it makes my weak. She's gorgeous, funny, amazing personality, basically the whole package. Today me, this girl, my friend and another mutual friend spent the day together and me and this girl and I really hit it off. She completely ignored my friend and spend the entire day flirting and joking with me. When we split off she called me and we spent about 3 hours talking on the phone. I'm completely convinced she feels the same way about me that I feel about her. Now my best friend was recently talking to me about seeing if he could actually date this girl or not and my advice on it. I am a loyal friend and don't want to do anything that would jeopardize our friendship but I als can't get this girl out of my head. Do I just forget about her because there is no way of making this transition? The only thing I can think of that would make this work is if I can get him to date someone else soon and then I could move in on this girl. Any other ideas?

So readers, what advice do you have for Stricken?

July 3, 2009 at 9:08 am
(1) Trevor H. says:

One thing is for sure: these feelings won’t go away unless you do something about them. It’s also pretty clear (if you haven’t realized it yet), that by dating this girl, you will be losing your best friend, which is never “worth it”.

Date someone else. Believe me, once you find some other girl to be interested in, you BEST FRIEND’S love interest won’t seem so important to you.

July 26, 2011 at 11:56 am
(2) Ahsan says:

today is great tomorrow is dremy

July 5, 2009 at 8:09 am
(3) Ari Kaplan says:

I think your feelings are lodged. Based upon personal experience and some stories I’ve read, it seems like you are in for a long-haul journey. Best of luck!

July 6, 2009 at 1:08 am
(4) Erin says:

Here’s an idea!
Tell your friend: I agree that this woman is amazing and I’m planning to ask her out. I know you two are not really together but I thought I’d be cool and at least let you know.

Tell this woman: I’d like to take you to dinner sometime and really get to know you better. How about Saturday night at Town Hall (just a suggestion if you happen to be in San Francisco).

You’re all adults. No one is committed. If the tables were turned, you’d have to be an adult about it. And besides, is just dinner. In the real world, when you actually get to know each other you might not even like her. And if you do like each other, then who cares about all this drama anyway?


July 6, 2009 at 8:18 pm
(5) Adam R-Z says:

Ahh Stricken… you have stumbled upon one of the clearest yet probably most unspoken man rules that exists: “Though shall not date thy buddies FB unless thoust gainst permission.”

It reminds me of a story I experienced in college. I had just broken up with a girl (lets call her Becky) that I had been dating exclusively for a couple months. Although I was the one to end the relationship, I still had feelings for Becky when we went our separate ways because she was a good person.

Shortly thereafter I was approached by a buddy of mine (let’s call him Ron) at a party asking if I would mind if he hooked up with Becky. He said they were good and drunk and hitting it off well. He wanted to know if it were cool if he made a move.

Because I still had feelings for Becky I told him I would feel uncomfortable. It probably had more to do with the fact I had one too many cocktails and was probably going home alone from the party, but nevertheless Ron respected my feelings and didn’t get freaky.

I highly respected Ron for his forthrightness (that is a word right?). He obeyed the clear but unspoken man laws that all guys agree to from puberty on.

Its now several years later and you know what Sticken? Becky is long gone. However, Ron and I are still buddies and I have never forgotten his respect for me. I even payed him back some years later by asking if I could hook up with his wife, to which he said “No” and I complied.

So Stricken – you next move is simple: Ask you buddy if you can make a move. If he says no, let it go. Lots more women in this world. If he’s cool with it, its all yours though you should really consider if want to hook up knowing your buddy has been there first. But that’s another story…

July 7, 2009 at 9:45 pm
(6) Peggy says:

After being married 4 times,I can tell you, the only reason you are so attracted to her is because you, want to TAKE HER AWAY FROM YOUR FRIEND, to try to prove your more of a man than he is. BAD IDEA, really bad idea. Go find a woman of your own. If you do suceed in taking her away from him, #-1- you will loose intrest in her real fast once you suceed in your quest,and
#-2- She will hate you for hurting her,and also
#-3 you will drive a wedge between you and someone you call a friend that will result in nothing but hard feeings and hurt for everyone involved.l
Move on, go find our own UN ATTACHED female,and leave your friens alone. TAKE MY ADVICE or don’t but don’t and you will regret it, I am 59 been threw almost everything.

July 8, 2009 at 2:43 am
(7) john says:

it may be you have some fellings for him and it’s good thing for you that you are dating with him so keep going and make a relation with him.

July 10, 2009 at 11:50 am
(8) JT$ says:

I thought I’d offer my story… An “ex” best friend of mine hooked up with my ex-girlfriend whom I still had feelings for/was trying to see if things could still work out with. He then lied to me about it. Long story short I don’t talk to either of them anymore and it was one of the most hurtful things I’ve ever been through.

The best you can do is approach everyone honestly about your feelings and intentions, that way everything is out in the open.

In the end I have to agree with Adam though that its one of those unwritten man codes (more likely it goes for both sexes) that you just don’t get involved with someone your friend is involved with. It will most likely not end well…

July 11, 2009 at 11:52 pm
(9) Dmoney says:

go for it man

July 12, 2009 at 6:20 pm
(10) Dan @ Tips for Flirting with Women says:

You will very likely be trading your friend for this girl. Unless you talk to him and he says it’s cool.

I would just say, “This girl’s giving me the deal… what should I do?” and let him frame it.

Read the subtext because he might say it’s okay but the tension in his body language disagrees.

What you’re looking for is a relaxed chuckle from him… and a go for it/dismissal of her at the same time. If you get anything else… you should consider it a swap and best… but most likely you will just lose them both.

July 31, 2009 at 11:04 pm
(11) Gman says:

Just tell him that you know this chick doesn’t (really) mean more to him than a piece of ass but to you she is more and you want to see her and will promise him that you will find him some other late night booty call to keep him satisfied. He will understand.

August 4, 2011 at 6:49 pm
(12) kelli says:

its all about communication. I totally 100 perc agree with gman. Talk to your friend, and see if he feels as passionate about her (looks personality the whole package). If he doesnt, then let him know how you feel. When a guy thinks a girl is the whole package, it is rare, and your friend will respect that. However, if your friend is crazy about her too, and wants more..then i wouldnt cross that line. You also need to think about the future. How might a relationship with her effect your relationship with him. Would you be able to deal with the fact that they have hooked up? Either way, im sensing that you are young, and there will be many more women that you will like as much, so be careful about messing up a good friendship. Good luck

August 8, 2011 at 10:32 am
(13) H says:

This may be a little different, but I figured I’d tell you my story. My current boyfriend, “Zack”, started to like me while he was in the process of helping his friend, “Tom”, try to get me. He wanted me to be happy and knew I liked Tom, so he worked hard to get us together. So eventually I started dating Tom and Zack started dating other girls. However, we kept contact and talked online. My relationship with Tom was a strange one. We only saw each other at school and the only time we did anything couple-like was on the bus. We dated for over a year though. After we broke up, Zack helped me through it. Then a month later he asked me out. We’ve been dating now for almost two year. Tom was angry at first, but now he still considers Zack a good friend still. Zack actually doesn’t like him all that much. This probably doesn’t happen in every situation but it could.

August 12, 2011 at 5:17 am
(14) Sticky says:

Id say share your feelings and talk with the homie first and foremost. Be real with him and respect his feelings

September 6, 2011 at 4:29 am
(15) Zero says:

I’d like to share a story I just experienced that relates to this topic. I also need advice on what move to make
Next and how to approach my supposed “best” friend. This weekend was my 23rd bday and I bought a suite at a very nice resort for me one of my good friends and two chicks, one of which I wanted to hook up with and the other was hooking up with my biddy who I bought the room for. My nest friend stayed at a cheaper place next to our resort. On the last night of the trip I passed out early and woke up to my nest friend being on the same bed with the chick I wanted hook up with in my hotel room. My best friend knew I was trying to get with her and came back to my hotel to hook up with her after I passed out. He doesn’t know that I know they hooked up and o can’t stop thinking about it. I don’t know what to do from here but I want to get it off my shoulders. What do I do

October 11, 2012 at 2:54 am
(16) jack is cool says:

look ask your friend first. no point in just making a move because they might say no and your friend might say no shes mine so think about it

good luck

December 8, 2012 at 2:37 pm
(17) Jordan says:

Ok, a few years back I was with this girl and had been for close to a year. I got off work early one day and went to cash my check. While I was there ppl were telling me that my best friend and her hooked up. I didn’t wanna believe it but I still sped home and sure enough I caught them cuddling. Her cheating is one thing but cuddling after was overkill. I eventually forgave both of them and he’s still my best friend. One of the few friends I have left. It’s been a few years but last night his girlfriend for the last 3 months tried hooking up with me. I saw it coming a mile away and almost consider it karma. I have a lot of self control so I was able to keep things from going too far, but she admitted that she knows it won’t work between them and asked for advice on how to end it. I don’t really know what to do. Should I help them split and go for it after? She’s already said she doesn’t really want anything with me besides a few nights of fun. That’s not my preferred “relationship” but recently it seems like that’s all I can hope for. I usually try to live with the view that I’d rather say I can’t believe I did that than I wish I would have. We only get one go around at this thing called life so why not live it to the fullest. Should I just go for it since he’s already betrayed me the same way?

January 6, 2014 at 10:49 pm
(18) esther says:

Making a relationship work is tough enough, but what if your best friend had history–messy history–with your new boyfriend or girlfriend? Could you handle the bad blood between the two most important people in your life? Do you have to deal with your friend’s unresolved feelings, or worse, your current boyfriend’s? Do you feel like you’re being forced to choose either a new love or an old pal? Or are you constantly worrying that something is still going on between people who claim their past is behind them?
If you’re stuck between your love and your friendship, MTV wants to hear from you! If you appear between the ages of 16 and 30, submit your story, complete with contact info and a picture to: datingex@mtv.com

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