Mothers, Sons and Potential Girlfriends

I have been working in an office for almost a year now, and everyone I work with and for is a good bit older than me. I am 25 and the youngest person, other than myself, is 40; everyone else is 55 and up. I happen to be dating around right now, and one of the women I work with has a son who is 21. He came into the office to use our copy machine, and we started talking. I assumed he was gay, but later in the week the woman I work with asked if it would be all right for him to Facebook friend me and get my number, because he wanted to take me to dinner. I said that I was kind of dating someone but am always open to new FB friends, because I didn't want to be rude. He is cute, and I'm super into dating everyone right now. He and I have started texting a bit, and he'd like to hang out. 

I don't technically work for this woman; I work for her bosses, but she does order me around a ton. Prior to this she has been the biggest challenge for me in the office, because she treats me like a child and is generally a rude and abrasive person. This has changed a little bit since her son asked for my info. Should I pursue this? Is this just too strange to be normal? Is it OK to date a 21-year-old if I am 25? If I do date this guy and it doesn't go super well, will she just get worse? I am trying to be very careful about this, but I also don't want to ditch out on a potentially interesting guy for dating or friendship purposes, just because his mom tries to run the office. 

I should also add that this job isn't my end-all-be-all. I will soon either be quitting to go to grad school, or I will be working at the office during the day and attending grad school at night, so I don't see my future at this particular office. Should I go for it? Should I even consider dating someone that much younger than me? Should I mix business and pleasure? What if he's a weirdo or we just don't have chemistry, and she gets even more intense? If I don't give him a chance will she be irritated by that? I've never been in a situation like this before. Rhonda, please help me navigate! Thanks!

Business and Pleasure

Career Advice: You say this job isn’t going to be your career, but it’s already on your résumé. Even if you pursue work in an entirely different field, you will still need to account for the time you’ve spent there. You also need this job to pay the bills for some time to come. Don’t jeopardize your references or your income because you’ve decided this job doesn’t matter. 

Dating Advice: Yes, you can definitely date someone four years younger. The question is really what stage of his life he’s in right now. If he’s in college and you’re working, the age difference will seem enormous. If he’s working, though, it will be a different story. Since you’re dating a lot of different people and it doesn’t sound like you have great expectations for this relationship, I don’t see any reason—strictly from an age standpoint—not to give it a shot.

On the question of mixing business and pleasure: Some amount of personal-professional cross-contamination is inevitable. It’s also desirable. You spend at least eight hours a day at work, so it will naturally be a place where you meet people—coworkers, clients, business partners, etc. The idea that they must not, under any circumstances, become your friends or know about your personal life is unnecessarily limiting. There’s room for some personal/professional overlap if you go about it in a circumspect way.

My concern is that your coworker will know more than you want her to about the relationship. Does he live at home? If so, she’ll always know if and when he comes home; she’ll have the opportunity to ask how things went, and so on. 

My advice: Date him if you’re interested, but be super-discreet about it. Don’t mention to his mom that you’ve spoken to, texted with or seen him. Don’t mention him to anyone around the office. When you’re out with him, act as though you’ve never met his mother, let alone worked with her for a year. It will feel a little strange at first, but I think that’s the surest way to keep your relationships and your co-workers separate.

Is It Okay To Fade Away?

I recently met a guy who asked for my number, then followed up with some texting, then we went out. The date was OK, not great, and I’m not really interested in seeing him again. At this point—after just one little date—is it OK to end things by not returning his texts? Calling him to say I’m not interested seems unnecessarily difficult and uncomfortable.

Distancing Myself

Sorry, DM, you can’t just fade out on this guy. You don’t have to go out with him again, but the considerate and adult thing to do in this case is to let him know, kindly, that you’re not interested. Even though you’ve only gone out once, you had some interactions—meeting, talking, texting—before that date, so there’s a little more to it than just that one date. If he’s still texting and contacting you, he’s still interested and thinking things might progress.

I find email ideal for this kind of thing. A short email saying that you enjoyed meeting him but don’t think the two of you are a match will solve the problem. It keeps him from getting his hopes up and keeps you from having to ignore his texts as they come in. If you don’t have his email address and he’s still texting you, you can say the same thing via text.

Not Invited

I have a long time friend who will be getting married in Massachusetts this fall. She and I used to be very, very close, best friends, really, but we’ve grown apart over the past few years. We never had any kind of falling out, just kind of went separate ways. I heard about the wedding second-hand and am really hurt that I wasn’t invited. I know we’re not best friends now, but we were once, and I still care about her and would certainly want her at my wedding. 

I saw her recently, and the wedding came up. She basically said that they were keeping the wedding small so that she and her fiancé could pay for everything without help and because they didn’t want to burden people with travel. She implied that it was pretty much family and one or two very close friends. But I know through the grapevine that it’s not really going to be the tiny affair my friend claimed. Am I wrong to be hurt by this? Is there any way to tactfully bring it up with my friend?

Left Out

I agree that being excluded this way would be hurtful, especially since it sounds like you really value the friendship you used to have. Bringing it up with your friend isn’t the right move, though. Weddings, guest lists and wedding parties are deals. (And, although all of this is deliberately manufactured by the wedding-industrial complex and the patriarchy) wedding planning is difficult, time-consuming, and stressful for a lot of people.

Sometimes, being a good friend means backing off when that’s what’s best for your friend. In your case, I think you act as the truest friend by not putting the bride-to-be in the uncomfortable position of having to explain her guest list or awkwardly offer you a late invite. You don’t want to add to her wedding-planning stress or strain her budget. What you can do is try to rebuild the friendship, if that’s what you want. Reach out to her to get together or get coffee or meet her new wife. It sounds like becoming closer friends might be what you’re really after.