The post title was the subject of the email exactly as it came to my inbox. That will be important later.
Hey there Captain,
I recently moved to a job that not only frees up more time to focus on schooling, but pays better. On the last day at my previous job, a girl I’d occasionally worked with and spoken with in the breakroom, asked for my number.
If her interest wasn’t obvious enough, as I walked out the door for the final time, her question was whether I had a girlfriend. I told her no, and to my amusement, her reply was that she’d text me. Needless to say, I got a text bright and early the next morning and we’ve been texting a bit.
She’s nice and I get along well with her, but I’m unsure about making the choice to date her. There are a few things I see as obstacles, but can be worked through.
She’s the daughter of my previous manager. Introductions as a boyfriend would be awkward because my manager didn’t want me to leave. I worked hard, kept a positive outlook, and somehow managed to get along with even the prickly people there. I lit up many people in that glum environment.
While texting, she obviously wanted to get to know me better, so I took the lead, organized a meetup, and we had fun, went for coffee, and wandered around the mall.
It was a great chance to get a feel for her personality, lifestyle, relationships, and maturity. When I asked her what she enjoys doing, she said that she didn’t really have any hobbies, but that she enjoys hanging out.
During the meetup, she spoke mostly about how she doesn’t like work, her parents are always mad at her, her exes (about two or three by how she spoke about them), and her life in general. After the meetup, she told me she had fun and wants to meetup again next week (the next free day she has).
Clearly she enjoyed my company if she already wants to hang out again. I asked what she wanted to do, and she said “I don’t know, I’m good with anything”. This bothered me somewhat, but I’m a big boy, not everyone knows how to be assertive.
When I asked whether she’s doing post-secondary, her answer was the generic “I hated school, so maybe I’ll become a cosmetician”. She agrees with whatever I say and doesn’t have a lot to say about her day, goals, or hobbies. That bothered me more deeply. I’m easygoing, so I spent time reflecting on why this information bothered me.
I have my life together. I’ve got a great part-time job to cover costs, university and my budget balances at the end of the day. I pursue hobbies such as photography, programming, hiking, and cooking. I’m on great terms with my family. I know myself well and what I want in a companion. This girl is wonderful, but it seems she dates as a form of entertainment; escape from her life. I date for a strong equal to share my interesting life with, and I’m not seeing a lot of that in her.
I’m not interested in being a crutch and I can’t save her from a boring life. If there’s a way for her to grow up and not rely on me to fill up her open schedule, I’m open to sharing a life with her. Although she’s my age (19), I don’t think she’s at the point where I can tell her this without grievously wounding her undeveloped ego, especially given how she admires me.
My first relationship (a different girl), about a year ago, ended because both of us had been insecure. Since then, I worked at self-improvement, and I’ve honestly been impressed with my progress. I’m a much more confident and relaxed person than I was.
I know myself well enough to know conversation is important to me. I’d feel lonelier in a relationship than alone if the other person had nothing interesting to talk about, AKA, their own life. I’m looking for a healthy relationship where our worlds don’t revolve around each other, but where we know there’s respite in each other’s company.
How can I kindly tell her that she’s wonderful and brave, but not ready to be the female lead in my story?
Casting a Female Lead
I’m glad you wrote to me before talking to this lady because you should not ever say the thing about how you’re “casting a female lead for your story” in a breakup conversation unless you want to be made fun of for decades, like the guy in college who told me that I wasn’t quite “First Lady Material*” after a private tour of the White House with his bigwig donor family, less than a month into dating him, on Valentine’s Day. He was and is a sweet man (and is happy as a clam with the First Lady of His Heart these days, as far as I know) but neither Twitter nor I will never forget his very earnest, deadly serious, incredibly detailed description of my lack of qualifications for a post I neither wanted nor knew I was running for. That day, I didn’t need to know all of his thoughts and feelings about me or how hard he struggled with his decision or the ways I fell short, I just needed to know the important stuff like, “This is over.”
Also, the self-love and self-confidence and interests you’ve worked so hard to develop are great, but referring to this woman as the “female lead in your story” and writing stuff like:
“I’m not interested in being a crutch and I can’t save her from a boring life. If there’s a way for her to grow up and not rely on me to fill up her open schedule, I’m open to sharing a life with her. Although she’s my age (19), I don’t think she’s at the point where I can tell her this without grievously wounding her undeveloped ego, especially given how she admires me.”
…is a real record-scratch for me. I think you are trying to show how thoughtful and empathetic you are being, but what’s coming across is so, very, very, very condescending. She is the lead in her own story, not a character in yours. Y’all went on one date. There is no need to magnanimously proclaim your “openness” to “sharing your life” with her or overdo it on reassuring us or her about how “wonderful” and “brave” she is or give us your “interesting”, university-educated resume & hobbies vs. her “vague,” “boring”, and “generic”cosmetology dreams.
It’s good that you can use a first date/hangout to really assess whether a person really fits with you, and it sounds like she does not! Feeling like you have nothing to talk about, or that the other person might be a bit too needy or more into going along with your plans than making their own are very good reasons to not go out again and thinking those things doesn’t make you a bad person. You are no doubt 100% correct that you and she are in different places in life. Finding out a little more about someone is what dates are for.
Literally all you have to do from here is to not go out with her again.
Since she already asked you out again and you agreed – enough to start making a plan – there is some backtracking to be done. Still, it is not impossible to bow out. Text her (yes, text) and say:
“I had fun the other day, and you are so sweet to ask me out again, but the more I think about it the more I don’t want to go on a second date. I’m so sorry I didn’t speak up sooner. I wish you well.”
Translate that into your own words if you want to, but make sure that you use the words “date” and “I don’t want to.”
Do not substitute “hang out” or “I can’t” and do not add on the words “right now.” You will be tempted to spare her feelings by being ambiguous and letting her down easy. Resist. If you are really worried about “grievously wounding her underdeveloped ego,” by not returning her feelings, the best thing you can do for her is to get out of her life quickly so that she can move on from thinking of you as a prospect for romance.
That means, if she texts back how she wants to just hang as friends, say, “What a nice offer, you’re so kind” but don’t accept the offer and don’t keep texting back and forth with her or planning “friendly” hangouts. If you are meant to be friends someday, it will be because common interests and acquaintances bring you into each other’s orbit. For now, let it drop.
I know this advice is coming with a whopping helping of “Jeez, get OVER yourself already, Fitzwilliam” but please know that there is love, here, too, for you, and for my younger self, and for my ex, President Earnest B. Forthcoming of The Republic of Sincerity, and for your coworker who was classy about waiting until the last day before she boldly asked you out. She will be just fine without you, and you both are most likely going to go on a lot more first and second dates with people who don’t quite fit with you. When that happens, say, “Thanks, but no!” and don’t try to sell them on your reasons.
*TRUE STORY, Y’ALL. And the year was 1996, so, it was sadly not an ironic Legally Blonde reference.