CautiouslyOptimistic Posted November 16, 2017 Share Posted November 16, 2017 (edited) I'm almost 45, female, divorced with two teens. The last man I dated, for ten months, was/is self employed as a contractor. (Our relationship ended last spring) While great at his actual job, he is pretty much an idiot when it comes to "office stuff." Not technology savvy. When he was marred, his ex wife did that side of the business, then when he divorced, his friend/pastor/counselor took over because he is smart in that area. When we were dating, I also helped him out with "getting things in order" with regard to QuickBooks and syncing his bank account, etc. We've kept in touch sporadically over the last several months since he owes me money from a home equity line of credit I took out to help him out/loan him money for his divorce settlement. (Not at all a bad situation because he pays me regularly, and even ahead). But, I know he's regretting the break-up and has even asked me out (I said no....this was a few weeks ago). He is a very nice man, very respectable, but I have no desire to reconcile romantically. Last night he texted me, asking me if he could call me. I was about to go to bed (early) so I said no, how about tomorrow. So today we talked. His "office help" is getting surgery that will take him out of commission for some time and he asked me to, before the end of the year, get his "stuff" in order because he just got a new computer and didn't realize his QuickBooks stuff from his laptop didn't reconcile to his new computer (which I think is a desktop). He needs help organizing everything so he knows where he stands with taxes. I'm very far from a QuickBooks expert since I don't use it, but I've figured it out for him before so I know I can again. He's going to pay me. I said yes. I need the money. I scheduled our appointment, at his home where his office is, for the first week of December. I'm not worried that he would ever disrespect my boundaries, but that he will read more into this. I really need this money, and I'd even entertain the idea of a future virtual assistant job for him on a regular basis, but is this a really dumb decision??? Am I sending the wrong message by saying yes even though I know he really does need office help? (I know for a fact he's incapable of doing this with his level of knowledge and expertise.) He lives over an hour away from me, FYI. Edited November 16, 2017 by CautiouslyOptimistic 1 Link to post Share on other sites
d0nnivain Posted November 16, 2017 Share Posted November 16, 2017 You need the money & you don't think he will disrespect your boundaries. If you are not longing for him back & especially if you can work outside of his presence, it might be do-able. I worked for an EX on a project basis once. It was one thing, lasted about 10 hours & involved us exchanging a few emails. He gave me the project. I worked on it. I sent the finished product back to him with an invoice. He paid me. That was our entire interaction & we had been broken up for over 20 years with both of us married to other people. I asked my husband before I took this assignment. He never told his wife which I thought was a little underhanded. Link to post Share on other sites
Author CautiouslyOptimistic Posted November 16, 2017 Author Share Posted November 16, 2017 Thanks, donnivain. We are both 100% single so there's nothing either of us would need to clear with anyone, but I still don't want to give the impression I am open to a reconciliation even if I want to do the actual work. Link to post Share on other sites
d0nnivain Posted November 16, 2017 Share Posted November 16, 2017 tell him that & set the boundaries of the work: location, hours, scope, compensation etc. Do not have lunch with him or after work drinks or anything like that. Just be aloof & professional. Cash your check & walk away. 2 Link to post Share on other sites
Author CautiouslyOptimistic Posted November 16, 2017 Author Share Posted November 16, 2017 tell him that & set the boundaries of the work: location, hours, scope, compensation etc. Do not have lunch with him or after work drinks or anything like that. Just be aloof & professional. Cash your check & walk away. Well, the thing is that the work is in his home office which is in a "bonus room" off his bedroom!! I'm also quite sure I'll be offered a drink....which I will not accept on principle . Link to post Share on other sites
d0nnivain Posted November 16, 2017 Share Posted November 16, 2017 Well, the thing is that the work is in his home office which is in a "bonus room" off his bedroom!! I'm also quite sure I'll be offered a drink....which I will not accept on principle . Ew . . . I don't know that I'd go there then. Can you work offsite & then just upload everything? Link to post Share on other sites
Author CautiouslyOptimistic Posted November 16, 2017 Author Share Posted November 16, 2017 Ew . . . I don't know that I'd go there then. Can you work offsite & then just upload everything? I asked him if I could do it remotely, from my home, but the issue is getting the stuff from his ancient laptop on to his new desktop. I guess it could happen if he took his whole desktop to a neutral location. ?? Link to post Share on other sites
Shining One Posted November 16, 2017 Share Posted November 16, 2017 I don't see a problem with it as long as you're not giving mixed signals. I work in IT and I've done a lot of technical work for various exes over the years. This often involved work in their homes, including the bedroom. A few tried to sweet-talk me into lowering prices, but that was it. Link to post Share on other sites
Author CautiouslyOptimistic Posted November 16, 2017 Author Share Posted November 16, 2017 I don't see a problem with it as long as you're not giving mixed signals. I work in IT and I've done a lot of technical work for various exes over the years. This often involved work in their homes, including the bedroom. A few tried to sweet-talk me into lowering prices, but that was it. Thank you! Link to post Share on other sites
alphamale Posted November 16, 2017 Share Posted November 16, 2017 if you need the money then go for it but make sure he knows the rules 1 Link to post Share on other sites
BarbedFenceRider Posted November 16, 2017 Share Posted November 16, 2017 So...he's a sweet man, but an idiot. Nice. lol I suppose if it was me, I would go to my bank and look for someone who didn't refer to me as the idiot. Credit Unions have plenty of resources for this kinda thing. Also, local community colleges with business and accounting classes are a great help. Then you wouldn't need to feel obliged to work for an idiot. And since he owes you money anyway, no extra debt between the two of you. If you need extra cash, try outside work or Uber. Fast, quick and pays well I hear. Instead of him having to relive the last 10 months, this would be the sensible thing to do. Then you don't have to get the creeps being near the bedroom and being offered alcoholic drinks. Yeah, it would be a lot better. Link to post Share on other sites
Author CautiouslyOptimistic Posted November 16, 2017 Author Share Posted November 16, 2017 So...he's a sweet man, but an idiot. Nice. lol I suppose if it was me, I would go to my bank and look for someone who didn't refer to me as the idiot. Credit Unions have plenty of resources for this kinda thing. Also, local community colleges with business and accounting classes are a great help. Then you wouldn't need to feel obliged to work for an idiot. And since he owes you money anyway, no extra debt between the two of you. If you need extra cash, try outside work or Uber. Fast, quick and pays well I hear. Instead of him having to relive the last 10 months, this would be the sensible thing to do. Then you don't have to get the creeps being near the bedroom and being offered alcoholic drinks. Yeah, it would be a lot better. Hmm, well he doesn't give me the creeps and he's not overall an idiot; I actually think he's quite intelligent in a lot of ways, like current events and politics. But, he is an idiot when it comes to secretarial/bookkeeping stuff . Link to post Share on other sites
BarbedFenceRider Posted November 16, 2017 Share Posted November 16, 2017 https://www.merriam-webster.com/dictionary/idiot Not to go all PC but... Link to post Share on other sites
Author CautiouslyOptimistic Posted November 16, 2017 Author Share Posted November 16, 2017 https://www.merriam-webster.com/dictionary/idiot Not to go all PC but... Thank you. I guess I should change my rhetoric. 1 Link to post Share on other sites
snflwrgrl Posted November 21, 2017 Share Posted November 21, 2017 Have you considered letting him know you are interested in the job but not in rekindling the relationship? If he still wants to hire you, you will at least know you are both under the same understanding. It may help you to feel better about taking the job too. I will be praying for you this week as you decide the best way to handle the situation. I wish you the best. Link to post Share on other sites
Gaeta Posted November 21, 2017 Share Posted November 21, 2017 I don't see anything wrong with it. You've dated him almost a year so you know he's an overall respectable man and he won't do anything innapropriate, right? You need the money, he needs someone he trusts. 1 Link to post Share on other sites
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