Tips for dating a busy entrepreneur/startup owner
June 30, 2016 12:00 AM   Subscribe

What are your tips for dating a busy entrepreneur/startup CEO who has very limited time and emotional energy? What are some tips to help me be more patient/understanding, and what can he do to make the situation better?

My boyfriend struggles with emotional unavailability due to being ridiculously busy and emotionally/mentally tired from being a CEO of a startup (he has been doing this for 5 years and his company took off). I struggle with feeling rejected because of this.
1. What can I do to be more supportive/understanding/patient?
2. What can he do to improve his emotional availability given that spending additional time together/talking more often is not an option?

More background:

I always hesitate to ask about personal relationships on here because every relationship is different, but this seems like a community of smart people who can help me generate ideas. First and foremost, please don't tell me to just DTMF -- I am aware that that is an option, and at the moment, I would like to explore ideas for making my current relationship work before I decide that there is no option but to DTMF.

I've been dating my boyfriend for about 7 months, and I think he's pretty great. He is smart, hardworking, can be very caring, and is generally a pretty awesome person. I am a very sensitive person and have struggled in the past with wanting control in relationships/anxiety and with trust that my partners are as emotionally invested as I am (which can really kill a relationship and has before in my case), and he struggles with knowing how to be more emotionally available in light of feeling busy, stressed, and mentally exhausted as a result of being a startup CEO/entrepreneur (which can kill a relationship and has before in his case). He started his company 5 years ago, and though it's really taken off, he still works a ton (late nights galore, paired with early mornings), doesn't sleep enough, etc.

He is very passionate about his work, and this is one of the things I admire about him. He makes time to see me as possible (we usually see each other one evening a week, sometimes two with friends (his or mine), and we usually hang out for the majority of a weekend day each week unless either one of us is out of town). Although I wish I could see him more, I have accepted that that isn't going to be what our relationship looks like for the foreseeable future. I can deal with this because I am also an ambitious person and should be spending the extra time working on my own life/career/hobbies anyway, and I've struggled with relationships taking over my life before, so in a sense this really helps me establish healthier boundaries. I've read up on others' experiences with dating entrepreneurs, and inevitably the time thing is a challenge, and the advice is consistently that partners should be very patient and supportive to make a relationship with an entrepreneur work.

What I really struggle with is that, in the time we do spend together, I don't feel like he is particularly emotionally available. While he is affectionate if I initiate, he is pretty bad about initiating shows of affection. He doesn't really volunteer emotional information; he'll respond when I ask, but the response is usually pretty limited. The relationship has progressed extremely slowly (think: 2.5 months of dating until first kiss happened), and he has admitted that he is afraid of committing too early, that previous relationships have ended due to what his exes termed "emotional unavailability," and that he is afraid of long term commitment because he thinks it could prevent him from achieving everything he wants to achieve with his life. Nevertheless, I've noticed that even when he'll tell me that his schedule is set and he can't see me more, he will make exceptions despite this. Even as we had the nth upset about all this last night, he agreed he wants to see me tomorrow evening even though it was not originally planned and he is going out of town the next day (and so will be extra busy wrapping up work/packing). I do feel like things have progressed -- very slowly, but I do see signs of deepening commitment on his end.

I admit I have my own emotional unavailability issues and am terrified of sticking this out because it might not work (this is a pattern for me). I am examining all this with a therapist. I also have to admit that one of my big fears that causes a lot of my emotional upsets in this relationship is the fact that I am now nearly 29, and I do want a family. I know all the rational stuff about how you can't just come up with a timeline for getting married, etc, but I know that this is a factor that is probably complicating this relationship that I need to figure out how to fix on my end. I don't know the guy well enough yet to say whether I would like to marry him someday, and I would definitely need a lot more time to even think about that. I do get nervous about the current state of our relationship because it is hard not to think about what trying to have kids and a life with someone so busy would be like. On the other hand, I would like to end up with someone who is an overachiever like me, so I know this might be one of those "choose your poison" types of situations.

Given that background, I'd like to hear from people who have dealt with trying to be patient with someone who is busy/emotionally semi-available and trying to work on it or who have been the busy/emotionally semi-available person and trying to work on it. It'd be great to hear from any entrepreneurs out there who have an idea what his lifestyle might be like. Of course, I am also asking him about this and thinking through this on my own for when we reconvene to talk about it, but I am looking to generate additional ideas I might not have thought of. Practical tips are super welcome.


1. What can I do to be more supportive/understanding/patient?
2. What can he do to improve his emotional availability given that spending additional time together/talking more often is not an option?

I know that ultimate it all comes down to choices, but I would like to give him a chance to learn if he does, in fact, want to. I would hate for someone else to rule me out because of things I am not great at, and lord knows I have my own relationship skills to improve.
posted by anonymous to Human Relations (19 answers total) 2 users marked this as a favorite
1. What can I do to be more supportive/understanding/patient?

What do you want in a relationship? If your needs are not being met,you are not required to be "more patient". He has a right to have his schedule, but you also have the right to have a relationship where you see the person X number of times a week, and they are emotionally available when you do see them.

If he's willing to change, that's great-but is he? Nothing you've written indicates that
s the case. It seems like you've already compromised a lot on what you want and I fail to see why you should compromise even more.

There are plenty of busy and ambitious people who also find time for a committed relationship; to me, it sounds like there's something beyond his work which is keeping him from committing ; whether that is a lack of desire to, or also being involved with another person/ people, I don't know. But those seem like likely possibilities from what I can gather.

That's just my take.
posted by bearette at 12:37 AM on June 30, 2016 [8 favorites]

PS- I've been in a relationship with someone who was emotionally unavailable and had little time for me. I felt like I was belittling myself and squeezing myself into a smaller and smaller box by telling myself that I also wanted "time to be independent" and "didn't need to spend that much time with him". He talked of spending more time together but never followed through. I later found out I was not the only person he was in a relationship with.
posted by bearette at 12:40 AM on June 30, 2016 [6 favorites]

Another way of looking at it that helps give perspective – and will do so for you too – is that being passionate about your work and seeing it as something you want to achieve in life, is the same thing as being emotionally invested in relationships and seeing a relationship and family as something you want to achieve in life.

This is not a message we're used to hearing, and when we do hear it, it tends to be "feminized" i.e. "this is something weak emotional women want." When really, it is just as important and literally vital (relationships and families are the things of life) as working, so why is it not viewed as such? Why is "investment" automatically interpreted as relating to money, when one can "invest" in relationships too? You can see the cracks in societal discourse when it comes to "networking". Why is "networking" seen as this clean, smart, businessy thing to do, when it is building relationships, i.e. the same thing everyone does? Because you're supposed to evaluate and utilize the value of your network? Uh, yeah, that's called maintaining relationships.

It's very much a shame, because white men as the privileged tend to get this full throttle and really have issues seeing relationships as something they're already doing in their careers (and thus could easily see as just as valuable in their personal lives), whereas we women, by dint of anything having the merest whiff of "relationship" being belittled, no matter how professional or societal-appearances-successful, tend to grok more easily that we're being sold a rotten bill of sale.

All that to say. Your boyfriend is aware he's emotionally unavailable in his personal life, okay, but is he taking concrete steps to get better at it? Is he identifying ways he can improve or is he counting on "upsets" to push him? You're seeing a therapist, and that's great. Has he considered it? Does he see the importance of it?

Regarding personal experiences. I too have dated ambitious men who claimed their work passion was what made them emotionally unavailable (as if their passion was something external and not their own internal motivations and choices...), and in both cases, yeah, the first ended up cheating on me with a woman he fell for (at work! ha!), and the second had been cheating the whole time, with/on several women, and using his job as an excuse.

I used to think I was emotionally unavailable, but years of therapy and a lot of soul-searching have shown me that I'm just very protective of my heart. I identified what it was about myself falling for unavailable men (in my case it was because I misinterpreted it as the guys being confident enough to respect my independence; once I met men who actually respected me, the difference became very clear), identified what I genuinely want from a relationship, and accepted that given the dominant social discourse where I live – it's quite patriarchal here – and the fact that men who are exceptions are always taken when I meet them, well, I too need to love and foster my independence. Men who claim they're emotionally unavailable and yet attracted to me, wanting me to give all the emotions, come up against my outstretched hand now. I'm still single at 40 and fine with that. I wanted a family as well; maybe someday I'll have one? I've looked into adoption and would be delighted to do that if/when I meet someone. For now I have a career I genuinely enjoy, awesome friends, and an enriching personal life.
posted by fraula at 1:39 AM on June 30, 2016 [12 favorites]

I am the busy sole owner of a young company. Most of my recent relationships have ended due to issues similar to those you describe - I work far too hard, to the detriment of my own physical and mental health, and to the health of my personal relationships. I have faith that when the right person comes along I'll give them priority over the company, but we'll see.

1. What can I do to be more supportive/understanding/patient?

As a thought experiment, imagine that he's the single parent of a young kid, instead of the CEO of a company. That's how I feel anyway - it's my job to keep this kid alive, I don't have someone to co-parent with, sometimes I can get a babysitter so I can enjoy a night out, but any time I'm out I'm dreading a call from the babysitter instead of truly being able to relax and enjoy my evening out. That might just be how I think about it, but perhaps thinking of it from that perspective may give you some insight.

2. What can he do to improve his emotional availability given that spending additional time together/talking more often is not an option?

This might just be me, but I'm far more emotionally available when I don't have access to my phone - it helps me stay present in the moment and focus on who and what are in front of me. I also genuinely LOVE doing new and exciting things, trying new restaurants, etc. but am too busy focusing on my company to keep track of what the new and exciting things in town even ARE. I can't plan a date to save my life... but on a good date that breaks me out of my status quo I come to life.

An anecdote that combines these things: one of the hardest nights of my life was when I skipped a company milestone event to attend a girlfriend's birthday dinner - and kept my phone on. Seeing all of the posts and photos about the milestone ruined my ability to engage and participate in the social event I was actually at. I felt guilty, like I was skipping my own kid's birthday to go on a date with someone I'd only known for a few months.
posted by adamk at 2:15 AM on June 30, 2016 [3 favorites]

Caveat: I may sound harsh this is meant kindly.

I am sorry but you should stop fooling yourself. You say you see your boyfriend once a week and every weekend (when you are in town), and yet this is not enough because he's not emotionally available even when you're together. You sound as if you admire this guy because he is an achiever who deigns to give you a little place in his life. It sounds like you are not his priority and so he is not willing to compromise on his work and life balance just for you. There will come a time when he meets someone whom he likes more than anything and you realise that he has managed to make himself emotionally available for her.

I know this is not what you want to hear but I'm sure he doesn't believe that you are the real deal. Yet. I may be wrong, and good for you if I am. But if you want to stay with him, you should embrace the relationship the way it is now.

Either that, or you ask him to marry you.
posted by Kwadeng at 3:54 AM on June 30, 2016 [8 favorites]

It took almost 3 months of dating for this guy to kiss you. It seems it's a hassle to get him to spend time with you and even when he does spend time with you he still makes the CHOICE to not be there with you mentally or emotionally.

This is wayy beyond just "emotional unavailability".

Usually I have more options to offer, but I'm sorry in your case, I have no other advice to give here than DTMF. I cannot see any universe where this ends with you thinking back on your time with him now and thinking "I'm so happy I took all that time out of my youth to spend with ____ rather than someone else."
posted by manderin at 4:53 AM on June 30, 2016

It's taken him months to kiss you, you initiate all affection, you initiate catching up, you plan your life around the crumbs of his time and affection when he deigns to give them to you...tell me, does he do anything at all? I dated this guy before, for eight years. Workaholic. Desperately waiting for the time when I would become a priority. Didn't eventuate. And why should it, he showed me all along who he was, I just didn't want to believe it. (After telling me for 8 years that we were going to get married, after we broke up, he admitted that yeah, that was never going to happen.)

Then I met my husband and within a year we were engaged. Because a man who really wants to be with you will show you. You won't be wondering where you stand or left twisting yourself into a pretzel trying to turn yourself into someone he wants. Look, I'm sure this guy likes you well enough to sleep with you when he can be bothered in between venture capital meetings but is this how you envisioned the great love of your life? Because every day you spend with this guy, is a day you aren't with the person who WILL treat you like treat you the love of their life.

And, no, you won't have to DTMFA. Just fade away. Start dating other men. I'm not sure this guy would even notice. I'm sorry to not give you the tips you want. Your story is well trodden ground and it rarely turns out well.
posted by Jubey at 5:11 AM on June 30, 2016 [14 favorites]

Most of my recent relationships have ended due to issues similar to those you describe - I work far too hard, to the detriment of my own physical and mental health, and to the health of my personal relationships. I have faith that when the right person comes along I'll give them priority over the company, but we'll see.

I think adamk's comment is pretty telling - if your boyfriend thought you were "the right person," wouldn't he be giving you priority over the company?

One of the best things I've learned to do for my own relationship is to prioritize that relationship, even though that involves making sacrifices. Knowing that my wife does the same means I know that our "us" is the most important thing to both of us, and that makes me feel wonderfully secure and loved. You deserve to feel wonderfully secure and loved, too.

I dunno - to me this doesn't seem like a great fit, and even in your question it sounds like you're grasping at scraps, seeing what you want to see rather than what's really there, and asking us to help you learn to disregard your own wants for the sake of this unavailable person. "Being patient" with someone who isn't giving you what you need is not a virtue. But I guess if you want to keep trying, maybe read some of the responses to this recent question from someone dating a surgeon, whose situation seems similar to yours? Pay particular attention to the people who describe living with doctors/surgeons and how they've had to manage that - and ask yourself if you would be happy living a life like that. If so, great, but it's okay if the answer is no.

Because again: being patient with someone who isn't giving you what you need is not a virtue.
posted by DingoMutt at 6:14 AM on June 30, 2016 [1 favorite]

If you married and had kids with this guy, you'd basically be a single parent. But worse, because you'd be doing all the emotional labor of maintaining your relationship with him, doing all the emotional labor of maintaining his family relationships and social life (how long until it's your responsibility to buy his parents' birthday presents), maintaining the household, all while you're a busy overachiever yourself. He hasn't shown any inclination to behave differently.
posted by Mavri at 6:26 AM on June 30, 2016 [6 favorites]

I'm not just going to say "dump this person." However, it is really on them to figure out how and whether they will be more emotionally available. Are they willing to devote as much energy to this as they do their job? Are they willing to go to weekly couples counselling?

For you, seeking patience, I think it comes down to "am I OK with how things are? and is this temporary or extending to the indefinite, possibly infinite future?"
posted by zippy at 6:36 AM on June 30, 2016 [1 favorite]

Seven months? If he was really in to you, he'd make time for you. He would, in fact, be neglecting his business for you. And he'd be emotionally available to you.

Don't settle for less than you deserve.
posted by MexicanYenta at 6:47 AM on June 30, 2016 [6 favorites]

Women are more complicated than men and that's why we often assume that when a man does certain things that it shouldn't necessarily be taken at face value. Because that's how we are.

But men REALLY are very simple creatures. If he doesn't have time for you... if you're the one to always initiate and suggest he take more time with you... if it takes several months of dating for him to just be minimally affectionate towards you... Then a smart woman takes this at face value and simply realizes he's not that invested in her or the relationship. And then she uses that VALUABLE time of hers to find someone who is rather than wasting it on him.

Just start dating other people. As someone suggested he probably won't even notice; and I'd be surprised if he wasn't already doing so himself anyway.
posted by manderin at 7:17 AM on June 30, 2016 [1 favorite]

My ex (with whom I have a child) was/is an entrepreneur, and based on my experience your boyfriend is unlikely to change. He values his work more than spending time with you or friends, and if you're not happy with how things are right now, you won't be happy a month or a year or 5 years from now. If it was going to change he would be scaling his work back now that the company is successful, but he's not. He's telling you this very clearly, he is not done achieving and doesn't want to be held back. The emotional unavailability (which goes together with how much he works) is not good for a longterm relationship. That he only spends more time with you when you kick up a fuss is not good, do you want to keep fighting for his attention?

The amount of time you spend together is reasonable for a dating relationship where both people have other major responsibilities or interests, but imagine having a child with him - it would be on you or on hired help (in the absence of family) to do all of the heavy lifting, he would not be available when the child is sick, or when you have a deadline and need him to take over. In our case we have family nearby thankfully, but it's still really hard because for him, his work comes first, having a child didn't change that at all (although he told me it would).

I think you should date other people, and consider learning to value and respect someone who works a more regular schedule, is stable, and is fairly content with how things are so they have the time and energy to take care of themselves, make you feel loved, build a life together, have kids together, because it sounds like that's what you really want. A more balanced partner could allow you to reach your goals and support you instead of both of you striving and then throwing kids into the mix.
posted by lafemma at 7:35 AM on June 30, 2016 [2 favorites]

This is sort of radical, especially on MeFi, but I find that increasing your love and respect for him is actually the way to go here. Stop thinking of him as "broken and bad at relationships, ignorant, and needing improvement." As long as you think of him that way, you will think that you can "fix him" and "fix the relationship" if only you come up with some clever hacks, wait for him to age and mature, or communicate your needs in a magical way he understands. This is wrong thinking, it is not really loving or kind, and it is, honestly, futile.

Practice radical acceptance instead. Think of him as perfect unto himself, as a fully individual, adult, conscious, intelligent being who has chosen his path in life. Respect that. Respect that he has chosen to dedicate his life to a career. You have chosen to dedicate your life to a balance of career and family, but as as your biological clock ticks, the balance may swing in favor of family. He is not on the same path as you, and that's okay. Also respect yourself, really get in touch with yourself, and fully appreciate your hopes, dreams and desires.

Neither of you is broken or bad at relationships or bad at compromise or needs fixing. You are both fine. Let him be free to be himself, and you be free to be yourself. And let him go if necessary. Communicate everything I just said to him, IE: "George, I really admire and respect that you have chosen to dedicate yourself to your difficult career. I wish you the best of luck. I have reached a point in my life where I want to start a family and devote more of my time and attention away from work to that end. To me, this is the most meaningful part of life and I can't continue to compromise on it. I would like to start seeing other people, what do you think?"

If this man loves you and doesn't want to lose you, he'll figure shit out right quick. If not, you've broken up gracefully with no hard feelings.
posted by quincunx at 7:45 AM on June 30, 2016 [8 favorites]

Running completely against the building consensus here...

First - I heartily second the radical acceptance suggested by quincunx. This is who he is. He has told you who he is, quite clearly. Expecting him to change completely is sort of unfair to him. To put it another way, the emotional unavailability is not a side effect of the entrepreneurship, it is a driving force.

Second - you asked for thoughts from mefites that are like this. I am in BigLaw, which is infamous for late nights and ridiculous work hours. And in my particular line of practice, I also run into a lot of the tech entrepreneurs. He's seeing you one or two nights and one full weekend day every week? Wow. WOW. That's a lot. That's a lot a lot. I was expecting one or two times a month. He's giving you more than he's got.

So building off of those two thoughts, consider accepting that this is who he is, and backing off. See him much less, and he will likely be able to be far more present for the times that he is there. If that isn't your cup of tea, then you should probably be seeing other people.

As some food for thought, I see really nasty divorces happen all the time. Almost 100% of the time, each party really thought that the other would change completely. One thought that the other would "really fall in love" and suddenly become emotionally available (and available in real space). The workaholic party was hoping that the other would come to accept them for who they were, or god forbid, would be happy/entertained by a baby and demand less of their time. (No, really!)

Please consider whether you two actually share the same values... you deserve someone who does.
posted by susiswimmer at 9:03 AM on June 30, 2016 [6 favorites]

I dated a serial entrepreneur for a couple of months (right as one of his businesses had just landed a several-million-dollar software contract, and the other was starting to take off). I'll tell you what I did: I broke up with him. He remains the only man I've ever dated where I initiated the breakup. Besides the business stuff, though, he seemed to put everything in his life ahead of spending time with me: his other friends, his athletic pursuits, etc. I had to call him once a week or so and beg him to let me buy him dinner just so I could see him. I could deal with him being a busy guy but not with the always-being-last part, although it sounds like you two are at least spending a decent amount of time together, so there's that. But is that enough for you? I used to actually CRY because I felt so lonely with him, lonelier than I've felt when I was single.

Right after we split up, I decided I was done with men and was going to focus on finishing grad school and finding a better job. Surprise -- within a few months, I met a great guy who wanted to spend lots of time with me and we've been together ever since, almost 10 years.
posted by jabes at 10:10 AM on June 30, 2016 [4 favorites]

I got married at 19 to another 19 year old. At the time, he had a part time job and I got a lot of his attention. It was part of why I married him.

Then, he joined the Army, which had been the plan all along, and began working 60+ hours a week. I got a lot less of his time.

I typically say that when we got married, he had a part time job and two full time hobbies and I was one of his hobbies. The other hobby was gaming.

We were friends for some years with a man who had a part time job and a full time hobby of gaming. He lived with his mother until she died when he was in his forties, and he inherited the house. I think after his mother died, he finally got a girlfriend.

Meanwhile, I was raising two kids and seeing the world as a military wife. No, I do not wish my husband had continued working part time in order to prioritize time with me. I got most of what I wanted out of marrying him.
If you want children, a man like you are seeing currently is a good bet for being able to provide for a family.

It takes 15 to 20 hours a week to establish and maintain an intimate relationship. It does not matter how that time is distributed. Doing most of it on the weekend is fine. My marriage defaulted to that, in part because of the long hours he worked.

It is also fine if some of those hours occur while doing other things. For example, if you dropped by his place to help him pack for his trip, you could shoehorn in some additional time together without adding to his stress.

When I was married, we usually had one car. A lot of conversation occurred while we drove him to work so I could keep the car. When we got two cars, the relationship deteriorated because we lost substantial built in conversation time.

You probably are not seeing him 15 hours a week. If you want this to work, you need to try to get in more time somehow. And, it will somehow need to be done in a way that doesn't subtract time from his job.

This will involve brainstorming. Can you meet him for breakfast? Can you stop by his office to bring him lunch and get 15 minutes of his time over lunch? Can you hit the gym together or not together or commute together?

It sounds like he is probably not hugely short of that 15 hours and like he is making a serious effort. I would try like hell to find some creative means to get more of his time in a way that didn't subtract time from his work.

This may well end up looking like the traditional wifely role of catering to him. Many people will tell you only a fool would do that. If people tell you that, consider if these are people who have successfully managed to do the married with kids and don't hate my spouse thing. If they are perpetually single or have zero plans to have kids, it is possible their attitude and their lifestyle are intrinsically interrelated.
posted by Michele in California at 12:47 PM on June 30, 2016 [2 favorites]

1. What can I do to be more supportive/understanding/patient?

Frankly, I don't think you're the issue here. Needing emotional availability is completely understandable and normal. I would contend that it's essential for most people. There is certainly room for compromise in relationships, but I think that's different from consciously suppressing your needs for someone who won't or can't meet those needs.
posted by cnc at 2:53 PM on June 30, 2016 [1 favorite]

What makes you happy?

I dated someone who had a ton of commitments. Gym, family, friends and work. He prided himself on being able to squeeze a minute and get six out of it. Example: we would have serious conversations while he was getting money out of the ATM etc. I didn't want to be a checkmark, I wanted more attention, and the resultant unhappiness, among other things, resulted in us splitting up.

Caveat emptor: I am a career woman and don't want kids and am not too opinionated on marriage. But I'm seeing someone now. And one of the things that makes me so happy is being a top priority. Which makes me want to make him a top priority. And enables me to overlook some minor things I would normally find disgruntling. It makes me feel like a queen (corny as it sounds) to know what he would sacrifice for me.

So, what do you value? Attention? Stability? His other qualities?

Would you be okay with weathering life's storms alone? Or maybe you might need a co-worker to be your listening ear when you're in the dumps, which could harm the relationship. You know best whether it could work out. And if you're asking this question, maybe you don't know, and need to do some soul searching. But definitely don't commit, emotionally or financially to this person before you're sure.
posted by kinoeye at 3:34 PM on June 30, 2016 [1 favorite]

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