How can I talk with my friend about his dating life given our history?
May 26, 2013 9:03 PM Subscribe
I have a very good friend who I spend time with on a regular basis. In recent history (and maybe probably for the foreseeable future) he has been depressed about his dating life, so naturally, it is a subject that comes up and I discuss it with him. However, given our past history together, it's been a really hard subject for me to discuss with him and I would like some help navigating this from the hivemind.
Me: Very very very happily married several years now to my ideal partner.
Him: Deals with depression. Single for quite some time now, very attractive handsome great guy with a lot going for him, but does have some personality quirks that make it both hard for him to find a match and make it hard for him to find and start relationships.
Our history: We dated twice. The first time I was very young and dumped him because I was young and flighty. Kept in touch. Saw eachother again years later and started dating again at my request. Were boyfriend and girlfriend for some time, but then I broke up with him again, mainly because I realized we were not compatible due to some differences in certain values and personality. I was also starting to fall for a different guy, who I am now married to. We did no contact for awhile, and then eventually started hanging out again as friends.
We hang out on regular basis as friends, he's friendly with my husband, and he's probably the second best friend I have. Like any friend, we talk about problems he is facing and stuff like that.
The problem I have is that since he is feeling depressed about his dating life and we talk about that, we talk about how he is feeling like he won't find somebody or his lack of confidence in what he has to offer. I tell him my honest feelings that he is a great guy with a lot to offer. But whenever I do that, there is this voice in my mind nagging at me saying that it sounds ridiculous coming from me, given that I dumped him twice! I really mean and believe everything I say, but it feels like our history is this giant elephant in the room making all my words and reassurances sound hollow. I've had the same conversation with other friends who were dealing with similar issues, and given that we had no history together I was able to reassure them without it seeming weird.
Given that he may be dealing with this issue for the foreseeable future, and I want to be there for him and talk about this with him as much as he needs to, I need some tips on how to talk with him when this subject comes up. What language, phrases, and words, and how do you (honestly!!!!) convey and reassure to someone you have ended a relationship twice that they are wonderful, datable, and desirable? How can I navigate these conversations gracefully?
Me: Very very very happily married several years now to my ideal partner.
Him: Deals with depression. Single for quite some time now, very attractive handsome great guy with a lot going for him, but does have some personality quirks that make it both hard for him to find a match and make it hard for him to find and start relationships.
Our history: We dated twice. The first time I was very young and dumped him because I was young and flighty. Kept in touch. Saw eachother again years later and started dating again at my request. Were boyfriend and girlfriend for some time, but then I broke up with him again, mainly because I realized we were not compatible due to some differences in certain values and personality. I was also starting to fall for a different guy, who I am now married to. We did no contact for awhile, and then eventually started hanging out again as friends.
We hang out on regular basis as friends, he's friendly with my husband, and he's probably the second best friend I have. Like any friend, we talk about problems he is facing and stuff like that.
The problem I have is that since he is feeling depressed about his dating life and we talk about that, we talk about how he is feeling like he won't find somebody or his lack of confidence in what he has to offer. I tell him my honest feelings that he is a great guy with a lot to offer. But whenever I do that, there is this voice in my mind nagging at me saying that it sounds ridiculous coming from me, given that I dumped him twice! I really mean and believe everything I say, but it feels like our history is this giant elephant in the room making all my words and reassurances sound hollow. I've had the same conversation with other friends who were dealing with similar issues, and given that we had no history together I was able to reassure them without it seeming weird.
Given that he may be dealing with this issue for the foreseeable future, and I want to be there for him and talk about this with him as much as he needs to, I need some tips on how to talk with him when this subject comes up. What language, phrases, and words, and how do you (honestly!!!!) convey and reassure to someone you have ended a relationship twice that they are wonderful, datable, and desirable? How can I navigate these conversations gracefully?
"You are a perfect partner for someone. I know that might seem silly coming from me, but you weren't the perfect partner for me. I assure you that many many people exist for whom you are the left partner," etc etc. Repeat as needed.
Though you are right that this advice is sort of odd coming from you. Is there anyone else he could hear it from?
posted by supercres at 9:36 PM on May 26, 2013
Though you are right that this advice is sort of odd coming from you. Is there anyone else he could hear it from?
posted by supercres at 9:36 PM on May 26, 2013
On how to talk to him: "You are a wonderful person. Just because we had differences does not mean you aren't worthy of a perfect partner."
Also, is there anyone else he can talk to about this? Honestly, I don't think you are the best person for it. No matter what you say to him, you can't change how he feels about it. I think he may need an more impartial party to deeply discuss this with.
For reference, I too had a long term guy friend that I had some intimate - non dating - contact with. I know he wanted to date, but we never did because I knew we weren't a match. I found a great husband, he would get bummed out by the types of girls he was dating and their rocky relationships.
I say this only because you also don't want to get into a situation where you are responsible for feeding his ego on how great and wonderful of a guy he is. You should be doing this for your husband. (I'm not saying you don't do that for your husband.) But it can be weird territory saying another man is amazing while you are married. It also, as you say, sends mixed signals to this guy for his self esteem.
Overall, put the focus on a finding match for him, not why you weren't a match for him. You aren't responsible for his happiness.
posted by Crystalinne at 10:16 PM on May 26, 2013 [1 favorite]
Also, is there anyone else he can talk to about this? Honestly, I don't think you are the best person for it. No matter what you say to him, you can't change how he feels about it. I think he may need an more impartial party to deeply discuss this with.
For reference, I too had a long term guy friend that I had some intimate - non dating - contact with. I know he wanted to date, but we never did because I knew we weren't a match. I found a great husband, he would get bummed out by the types of girls he was dating and their rocky relationships.
I say this only because you also don't want to get into a situation where you are responsible for feeding his ego on how great and wonderful of a guy he is. You should be doing this for your husband. (I'm not saying you don't do that for your husband.) But it can be weird territory saying another man is amazing while you are married. It also, as you say, sends mixed signals to this guy for his self esteem.
Overall, put the focus on a finding match for him, not why you weren't a match for him. You aren't responsible for his happiness.
posted by Crystalinne at 10:16 PM on May 26, 2013 [1 favorite]
very attractive handsome great guy with a lot going for him, but does have some personality quirks that make it both hard for him to find a match and make it hard for him to find and start relationships
You say you've been honest with him about his good qualities. Have you found a way to be honest with him about his quirks? Your reassurances might sound less hollow (to you, but also to him) if you could acknowledge both that he's great in a lot of ways, AND that he's having a rough time of dating for X, Y, Z reasons. It may be especially helpful to him if these quirks, whatever they are, are things he's not aware might be getting in his way. It's your call as to whether he's open to hearing your opinion on that, but since he presumably wants to talk about his difficulties, maybe he would be open to feedback.
posted by Dixon Ticonderoga at 10:35 PM on May 26, 2013 [1 favorite]
You say you've been honest with him about his good qualities. Have you found a way to be honest with him about his quirks? Your reassurances might sound less hollow (to you, but also to him) if you could acknowledge both that he's great in a lot of ways, AND that he's having a rough time of dating for X, Y, Z reasons. It may be especially helpful to him if these quirks, whatever they are, are things he's not aware might be getting in his way. It's your call as to whether he's open to hearing your opinion on that, but since he presumably wants to talk about his difficulties, maybe he would be open to feedback.
posted by Dixon Ticonderoga at 10:35 PM on May 26, 2013 [1 favorite]
I would trawl through previous relationship AskMeFis on the subject and quote the advice others have been given. Previous posts from people wanting to know how to meet the perfect partner/sick of dating but miserable alone/not sure how to meet people after x time off the dating market etc - that kind of thing. Many of them stress the need to seek out activities that build confidence, get you out there meeting people (not necessarily dating/bar-hopping), increase skills/self-development, feeling more accepting of the self, that kind of thing. Unsurprisingly, many of these activities are suggested to people feeling depressed as well. This is at least partly because if you're not okay/happy with yourself, you're not likely to be very good at attracting a partner either.
Talking about concrete things he could be doing to feel better about himself as a person - focusing on the depression angle - could be a way in for you. That way the focus is on getting him to the stage where he's happy with himself and then won't require you to tell him that he is sexy and desirable and would be great at making the ladies happy, which really isn't your job.
I'd also suggest being upfront with him about this. Pick a good time when he seems to be doing well and isn't too miserable and just explain that it's easier for you to focus on specific solutions to improve his sense of happiness with himself rather than give him non-specific reassurance about his desirability. Then work with him on how you can support him in his journey while not feeling incredibly uncomfortable on your own.
posted by Athanassiel at 12:25 AM on May 27, 2013 [1 favorite]
Talking about concrete things he could be doing to feel better about himself as a person - focusing on the depression angle - could be a way in for you. That way the focus is on getting him to the stage where he's happy with himself and then won't require you to tell him that he is sexy and desirable and would be great at making the ladies happy, which really isn't your job.
I'd also suggest being upfront with him about this. Pick a good time when he seems to be doing well and isn't too miserable and just explain that it's easier for you to focus on specific solutions to improve his sense of happiness with himself rather than give him non-specific reassurance about his desirability. Then work with him on how you can support him in his journey while not feeling incredibly uncomfortable on your own.
posted by Athanassiel at 12:25 AM on May 27, 2013 [1 favorite]
What language, phrases, and words, and how do you (honestly!!!!) convey and reassure to someone you have ended a relationship twice that they are wonderful, datable, and desirable?
If you really care about this friend, don't you think it's better to be silent in the face of his insecurity? That way he can become the man he needs to become rather than retreating to your nest of support. The inescapable reality is that he needed to be a better man to keep you; treat him like a man by letting him feel it.
But don't tell him how to grow. It's no longer your role to be specific, or give advice. He has to discover his own voice, his own desire, his own masculinity.
On your side, what do you think motivates your need to reassure him? Is it that you really care about him, or is it that you selfishly want him to develop a dependence on your support?
posted by esprit de l'escalier at 1:32 AM on May 27, 2013
If you really care about this friend, don't you think it's better to be silent in the face of his insecurity? That way he can become the man he needs to become rather than retreating to your nest of support. The inescapable reality is that he needed to be a better man to keep you; treat him like a man by letting him feel it.
But don't tell him how to grow. It's no longer your role to be specific, or give advice. He has to discover his own voice, his own desire, his own masculinity.
On your side, what do you think motivates your need to reassure him? Is it that you really care about him, or is it that you selfishly want him to develop a dependence on your support?
posted by esprit de l'escalier at 1:32 AM on May 27, 2013
I'm going to take a slightly different tack to everyone else and suggest that you don't start with any mention of how you and he got on. Instead, look at this way:
It's difficult to be happy with someone who's not happy with themselves. His priority numero uno is to tackle his depression, it will positively affect his dating life. Speaking as someone with a certain amount of experience in that respect, I can tell you that telling him he's an awesome guy isn't going to help because his depression-brain will respond either "clearly not THAT awesome or someone would be dating me" or "I know, but so what? It doesn't get me anywhere".
Potential partners who feel good about themselves can pick up on this, I've found, it's like some huge big klaxon and flashing lights saying "This dude does not have his shit together". Tell him that feeling bad about himself makes it harder for people to see how cool he is, and that he needs to tackle the negativity as the first step. Once he's done that, he'll be in a much better place to accept that some people just aren't a good fit, and that doesn't mean anything about whether they're awesome people or not.
posted by fearnothing at 1:33 AM on May 27, 2013 [2 favorites]
It's difficult to be happy with someone who's not happy with themselves. His priority numero uno is to tackle his depression, it will positively affect his dating life. Speaking as someone with a certain amount of experience in that respect, I can tell you that telling him he's an awesome guy isn't going to help because his depression-brain will respond either "clearly not THAT awesome or someone would be dating me" or "I know, but so what? It doesn't get me anywhere".
Potential partners who feel good about themselves can pick up on this, I've found, it's like some huge big klaxon and flashing lights saying "This dude does not have his shit together". Tell him that feeling bad about himself makes it harder for people to see how cool he is, and that he needs to tackle the negativity as the first step. Once he's done that, he'll be in a much better place to accept that some people just aren't a good fit, and that doesn't mean anything about whether they're awesome people or not.
posted by fearnothing at 1:33 AM on May 27, 2013 [2 favorites]
Does your advice seem weird to him? You say it feels hollow to you given your history, but it isn't about you, it's about him. So just take yourself out of it and be there for your friend.
If the reasons you were incompatible are the same things getting in his way now, then just be straight up about that, it's a valid experiential reference for him. But beyond that your history is nothing more than the path that's gotten you to the friendship you have today. So be there as his current friend, not as his former girlfriend. If that's not possible, you need to step back.
posted by headnsouth at 4:58 AM on May 27, 2013
If the reasons you were incompatible are the same things getting in his way now, then just be straight up about that, it's a valid experiential reference for him. But beyond that your history is nothing more than the path that's gotten you to the friendship you have today. So be there as his current friend, not as his former girlfriend. If that's not possible, you need to step back.
posted by headnsouth at 4:58 AM on May 27, 2013
I am confused as to who needs whom here?
If is problem is that he's depressed, he doesn't have a relationship problem, he has a problem with being depressed. The relationship he needs to focus on is the relationship with himself. I don't see how one is depressed about their dating life, as depression usually doesn't limit itself to one aspect of life. It may be exhibiting itself in his dating life, but lots of people don't date and are perfectly happy. Lots of depressed people have relationships. So actually, none of what you said makes any sense to me.
Secondly, you dated him, dumped him twice and now he's friendly with your husband, and depressed about his dating life? It sounds like he has some things to sort out, and I wonder if you are doing the opposite of helping. Perhaps you are a constant reminder of his dating failures. You may see a friend, but you could be friends with a lot of people. Maybe he's still carrying a torch for you. Maybe he can't move on because his (ex-girl)friend treats him as a pity case.
This sounds like a very weird problem to have. The only problem that I see is he needs to go meet new women, and not spend time with ex-girlfriends who are married to other dudes that he was dumped for.
If you're really this guy's friend, maybe it's time to let him go and let him sort himself out.
posted by nickrussell at 8:22 AM on May 27, 2013 [4 favorites]
If is problem is that he's depressed, he doesn't have a relationship problem, he has a problem with being depressed. The relationship he needs to focus on is the relationship with himself. I don't see how one is depressed about their dating life, as depression usually doesn't limit itself to one aspect of life. It may be exhibiting itself in his dating life, but lots of people don't date and are perfectly happy. Lots of depressed people have relationships. So actually, none of what you said makes any sense to me.
Secondly, you dated him, dumped him twice and now he's friendly with your husband, and depressed about his dating life? It sounds like he has some things to sort out, and I wonder if you are doing the opposite of helping. Perhaps you are a constant reminder of his dating failures. You may see a friend, but you could be friends with a lot of people. Maybe he's still carrying a torch for you. Maybe he can't move on because his (ex-girl)friend treats him as a pity case.
This sounds like a very weird problem to have. The only problem that I see is he needs to go meet new women, and not spend time with ex-girlfriends who are married to other dudes that he was dumped for.
If you're really this guy's friend, maybe it's time to let him go and let him sort himself out.
posted by nickrussell at 8:22 AM on May 27, 2013 [4 favorites]
I think you should stop worrying about your history with this guy—it's not relevant unless he makes it relevant. In other words, if he explicitly says "Why should I believe you? You dumped me twice!" then you need to deal with it; otherwise just treat him as a friend who needs reassurance. Having been on both sides of this, my experience is that people who are having trouble finding a mate are far more focused on the present and immediate future than on the past. Just try to make him feel good about himself and point him in the right direction.
As for you people saying things like "he needs to go meet new women, and not spend time with ex-girlfriends who are married to other dudes that he was dumped for": it sounds like you're saying it's impossible for an ex to be a friend, which is ridiculous. These people are close friends, and that's what matters, not their past relationship.
posted by languagehat at 12:11 PM on May 27, 2013 [1 favorite]
As for you people saying things like "he needs to go meet new women, and not spend time with ex-girlfriends who are married to other dudes that he was dumped for": it sounds like you're saying it's impossible for an ex to be a friend, which is ridiculous. These people are close friends, and that's what matters, not their past relationship.
posted by languagehat at 12:11 PM on May 27, 2013 [1 favorite]
it sounds like you're saying it's impossible for an ex to be a friend
Not saying that at all. Just saying that all sources of potential influence should be investigated. If the problem is romantic depression, then it seems worthwhile to investigate the influence of a close friendship with an ex who terminated a romantic relationship twice.
posted by nickrussell at 2:59 PM on May 27, 2013
Not saying that at all. Just saying that all sources of potential influence should be investigated. If the problem is romantic depression, then it seems worthwhile to investigate the influence of a close friendship with an ex who terminated a romantic relationship twice.
posted by nickrussell at 2:59 PM on May 27, 2013
This thread is closed to new comments.
I really do mean what I say. Keep going, okay? You'll find her."
posted by These Birds of a Feather at 9:07 PM on May 26, 2013