Happy February! It’s my first Ask Kelly of 2023, and I have three totally different questions for you this month. I’ve been enjoying winter in Minnesota more than I thought I would (it’s been very mild, as I’m writing this, it’s 40˚ and raining!) but I’m really looking forward to spring. I was just in California a few weeks ago to do some wedding planning, and I’m feeling so good about how it’s all turning out. You can read more about it here if you’re curious. Thanks so much for all your lovely feedback on December’s issue, which was a long one about deciding whether or not to have kids. I love hearing from you all, so keep it coming!
If you have a question for my next edition of Ask Kelly, submit it here.
Hi Kelly!
At the beginning of the pandemic, my brother started dating a girl from my hometown (we’ll call her Sarah). My sister and I live together across the country from where we grew up, and given the pandemic times, neither my sister or I have spent much time back at home and unfortunately also haven’t gotten to know Sarah very well, either. Fast forward, my brother is now engaged and is excited to be celebrating via a beach destination wedding abroad this upcoming summer. As wedding planning kicked off, all the normal details started falling into place, including Sarah recently asking her bridesmaids to be a part of the day.
Here’s where my question comes in. Sarah asked a handful of her friends–and my sister and I–to go wedding dress shopping with her recently. My sister unfortunately couldn’t go, but I was back home for a visit and did make it to the shopping appointment. Sarah was thrilled to use this time to ask the group of girls and I all to be her bridesmaids for the wedding, with cute custom gift bags and all!
As the weeks have unfolded, I was really hoping my sister (the third and only other sibling) would soon hear something to be a part of the day too. Unfortunately, they’ve since confirmed the wedding party and moved forward without the inclusion of my sister. While I totally understand that bridal party details are a very personal decision and should be based upon the close relationships the couple holds with each person, it just doesn’t feel right that I was asked to be in the bridal party and my older sister wasn’t, given our very similar relationship to the bride. It just really is a bit bizarre and a pretty even “playing field” here!
My sister and I live together, will be traveling in for the wedding together, staying at the resort together, and I really don’t want her (the only sibling who is also single and on her own) to feel excluded and just secretly disappointed. Overall, it really makes things just more complicated and kind of takes the fun out of it all. As it’s still early in the planning, I continue to question how this day will feel for all parties and am considering how to approach it thoughtfully.
If this were you, what would you do? Continue on course as a bridesmaid and just celebrate my brother and his fiancée as an official member of the bridal party, or politely find a way to step out of the bridal party obligation and partake as a regular guest with my sister and the rest of the family? – Kenzie
Dear Kenzie,
Welp–this is quite the predicament! I literally *just* picked a wedding dress on the day I saw your question come in, and it felt fitting that I try my best to answer it. I totally understand the dilemma here. In fact, this is partially the reason I’m choosing to forego a bridal party for my wedding altogether. There are just too many politics involved with choosing bridesmaids. Feelings too often get hurt, and people get left out. This sort of “forced ranking” of friends and family just feels too difficult to me–especially as I get older–and so many of the people in our would-be bridal party are parents to small children. This isn’t your wedding, though, and you’re not in control of the situation, so I can understand why you’re feeling like Sarah’s choice was a bit bizarre! For what it’s worth, I agree!
If this were me, the first step I would take is asking my brother–soon!–if he has any insight to share. Their wedding is this summer, so you need to act pretty quickly if you’re going to bring this up to him. It sounds like, had your sister been present that day to shop for a wedding dress, she would have been included in the bridal party. By missing that one important event, did it disqualify her from being a bridesmaid? If so, why? Was there ever an implication that by missing the appointment, your sister wasn’t “invested” enough to be asked? I have lots of questions here!
I’d also find out if your sister’s exclusion from the wedding party was just a numbers game. Because bridesmaids and groomsmen usually walk down the aisle together, there is often an even number of them. That being said, I’ve seen it more than once where a groomsman will walk with a bridesmaid on each arm, and no one thinks it’s weird at all! It’s actually kind of charming. It may be easier for them logistically to add another bridesmaid, rather than have you drop out. Then there will probably be one too many groomsmen, which I can’t recall having seen before.
By (gently) talking to your brother (alone), I’m hoping you’ll gain a better understanding of their decision making process. It’s their wedding and they can decide to do whatever they want, but you are not obligated to be a bridesmaid. Being a bridesmaid often incurs extra expenses, and certainly an extra time investment. Since you’re not super close with the bride, my guess is that you want to participate and support your brother on his wedding day, but not at the expense of your sister.
You’re right in assuming that, if you’re in the bridal party and your only other sibling is the one getting married, your sister may feel really left out. She may spend a lot of the weekend hanging out with your parents, which I’m sure would be fine, but probably not the fun weekend she was envisioning at a destination wedding on the beach somewhere! I’m getting the sense from your question that you might actually have a better time as a regular guest with your sister and the rest of the family. Maybe there is another friend Sarah didn’t include in the initial group who could take your place. Take your brother out for lunch, if at all possible, or ask if you can FaceTime him. Delicately chat with your brother about all of this, and reassure him that you just want to make sure everyone has an awesome time. Stay open to any other solutions he may offer that I haven’t suggested here, and I know you’ll figure this out. Best of luck!
x Kelly
Hi Kelly–I am in a situation I have never experienced before and could really use some help! A little bit about me: Early 30s; have not been on a date or had a boyfriend in over 10 years; at my job for almost a decade. My dilemma is that I have developed feelings for a colleague I work with closely every day. He is a good man and checks off all my “boxes” so far. I am really enjoying getting to know him and we have only worked together for a few months. Should I make some kind of move? Do I drop a hint (and how would I do that?!)? Should I wait for him to make a move? Should I forget the whole thing and move on? The whole thing feels very risky but at the same time I feel like he would be worth it. Please help!! –Eleanor
Eleanor!
This is such a tricky one!!! The *very* first thing to do is check with HR to see if they have any policies around dating at the office. For the purposes of this column, I’m going to pretty much assume that it’s generally okay with HR, but do make sure you actually check before you do anything.
So! An obvious pro is that you haven’t dated anyone for a long time, and you like this guy! He checks all your “boxes,” and he seems to be a nice person. You’ve gotten to know him through work and like everything you see so far. All of this is really promising.
However! You work with this person. In almost every case, I’d say “you have nothing to lose” by asking someone out, but that isn’t true here. If you make a move and it’s not reciprocated, things might be a bit awkward from here on out. You’ll either have to endure the awkwardness every day until it naturally fades, or possibly leave your job if it never does. Best case scenario, you start dating, but one of you might have to leave the company or move departments, depending on the specific policies set by HR (if there are any, obviously I don’t know the details). Same for if you start dating and then break up.
I guess my question is: How high is your tolerance for awkwardness, and how much do you like your job? My advice hinges on these questions. If you absolutely love your job, I would probably do nothing and see if he makes a move. I would hate for you to potentially have to quit a job you love over some guy, or have your daily work life tainted by this not working out. However, if you’re in a take-it-or-leave-it scenario with work, I say take a risk! Ask him out!
I’d suggest something simple and casual. If you interact with him regularly, perhaps something easy like “Hey, there’s a new coffee shop down the street I’ve been wanting to try, want to go with me next week?” Going out to lunch somewhere you’ve been wanting to try or for a drink would work too. Or, you could start by inviting him to a group thing you’re already doing with some other people, like going to a trivia night, and see how he responds.
See how it goes outside of a work setting and if you’re feeling a vibe! If you are and you think he might be too, then you could ask him on a more obvious date (dinner after work?) if he doesn’t make a move within a few days. Just be super polite if he says no or makes an excuse. Good luck!!!
x Kelly
Dear Kelly,
I am a queer person in my mid-twenties who happened to fall for a cool, great guy three years younger than me. It took me completely by surprise, not in small part because in the pandemic era I was mostly online dating and therefore able to narrow really specifically to the types of people I thought I’d be most compatible with: women, other queer people, very very leftist, my age or older, and so on. While most of those people were great (and I genuinely made at least one friend!) I found that I was mostly vibing with them based on similar interests and identities and not necessarily actual chemistry. Enter my guy. We’re in the same graduate school, and I made the first move. Our chemistry is off the charts, but I had extremely firm boundaries up–I told him the first night we hung out that I’d never date a cis-straight guy. Lo and behold, though, I slowly fell for him hard, and after four months of “casual,” we officially “got together” six months ago.
Here’s the rub, though. Any issues we have stem from those “not fitting into my boxes” areas–slightly different political stances, gender debates, and communication issues that I attribute to his gender and differences in life experience–he’s 24 to my 27. I can’t help but have this constant, quiet wonder if I would be happier with another woman. Isn’t the best part of being queer not having to navigate these tensions, because I get to share those identities with my partner? Any time we get into a disagreement, I immediately start wondering if that disagreement would occur if I was dating another queer person. I know the answer isn’t necessarily yes, because I’ve dated other queer people and had some awful relationships, but I still look at my lesbian friends’ partnerships and feel jealousy over their communication, friendship, and deep understanding of each other. I don’t like feeling that I have one foot out the door, but I also wonder whether staying in this mindset is unfair to both of us. We are graduating soon and I am moving out of state; he doesn’t yet know where he’s going. Right now, we’re vaguely planning to try to stay together, but without anything concrete worked out. Should I push through and try to figure out “forever” despite these questions? –Anonymous
Dear Anonymous,
Thank you so much for asking me this question, even though I’m not totally sure I am qualified to answer it! I’m going to try my absolute best, and you can take it or leave it. 🙂 I loved your question especially because I have coincidentally been chatting with a friend who is dealing with a similar dilemma with her boyfriend. They’re older and more established in their relationship, and the stakes are a bit higher as there are signs of an engagement right around the corner, but the parallels are noticeable. She is a (privately) queer, extremely liberal woman dating a straight, cis man who is a Republican, and we’ve explored the complications that come with that dynamic over the past few weeks.
It sounds like, though you have amazing chemistry and have fallen hard for each other, you’re sensing that maybe you’re just too different to have a future together. Wanting a partner who is on the same (or at least similar) page as you politically, who understands you and makes you feel seen rather than debating with you about gender differences, is very understandable! They say that opposites attract, but whether that attraction is a solid foundation for a relationship that will go the distance is less clear.
In my opinion, these issues are big enough to bring up in a conversation with him before you move forward and figure out if he will follow you out of state after graduation. As a cis/straight woman myself, I recognize that I can’t entirely relate to the struggles you’re facing. But what I can do is pose a series of questions that I hope will help you get to the bottom of your dilemma:
- Are the issues you’re referring to that are causing you to question your relationship–political differences, gender debates, and communication styles–non-negotiables for you?
- Do you think that he could/would change if he knew how important some of these things are to you? Is he the type of person open to adjusting his way of thinking if he knew it was hurting you?
- How big of a role would you like chemistry to play in your relationship? Is chemistry more, less, or equally important to you as someone fitting in to your “boxes”?
- Do you feel like your partner is your best friend? Is that the kind of relationship you’re looking for?
- Does he know the extent to which you’re questioning the relationship? If not, how do you think he would feel if he found out?
- Do you think he will ever be able to really understand you? And would you be okay with it if he never did?
I’m not completely sure that the issues you have stem from your partner’s gender (maybe a bit from age, for sure). You certainly don’t have to be queer to be accepting (and encouraging!) of another person’s gender identity or sexuality. There are plenty of cis, straight men who are as left as it gets politically. And any 24-year-old person is probably still working on their communication skills. I mean, aren’t we all?? Age alone is something that, obviously, will get better in time. Ten years from now, if you stay together, your age difference probably won’t seem very significant.
You may indeed be happier at the end of the day in a relationship with a woman, but like you said, you’ve been in queer relationships that have been awful too. Regardless of their gender, age, or political affiliation, make sure you’re with a partner who celebrates you. You deserve to feel heard, respected, and understood, especially if you’re at the point where you are considering “forever.”
x Kelly
