# Romantic, stupid, or just creepy? You decide. **URL:** \ **Category:** In My Humble Opinion\ **Created:** [March 19, 2007, 5:22pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588 "2007-03-19T17:22:50Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 5:22pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/1 "2007-03-19T17:22:50Z")
I think I already know the answer to this, but it’s good to have a sounding board. Since the day I started at this job, I’ve been head-over-ears fascinated with one of my coworkers. I spend a lot of time thinking about her. And it seems that she is, or was, a bit flirtatious with me. Asking her out seemed like a bad idea, as my girlfriend and her husband probably would not have been cool with it. But we’ve dispensed with those losers. So anyway, last week I completed my latest painting. I e-mailed an image of it to various coworkers who are fans of my stuff. It was universally acclaimed by every one of them. I rather like it myself, and wonder if it couldn’t fetch $250 in a gallery. The lovely lady in question especially gushed over it. So I was thinking – good idea to frame it and give it to her? Or would I just come off looking like a desparate fool that can’t get a date outside of my own office? Or should I just man up and ask her out already? ---
**Author:** ![Beadalin](https://avatars.discourse-cdn.com/v4/letter/b/3be4f8/32.png) [@Beadalin](https://boards.straightdope.com/u/Beadalin)\ **Post date:** [March 19, 2007, 5:32pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/2 "2007-03-19T17:32:56Z")
It’s a lovely idea… for later. It’s more appropriate as a somewhat large romantic gesture for a romantic partner, not someone you hope to woo. Ask her out for coffee or some other short activity first, to see if she’s receptive to dating. Once you’ve been going out for a month or so you could consider giving her the painting. Good luck! ---
**Author:** ![Kalhoun](https://avatars.discourse-cdn.com/v4/letter/k/3bc359/32.png) [@Kalhoun](https://boards.straightdope.com/u/Kalhoun)\ **Post date:** [March 19, 2007, 5:34pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/3 "2007-03-19T17:34:33Z")
[QUOTE=tdn] I think I already know the answer to this, but it’s good to have a sounding board. Since the day I started at this job, I’ve been head-over-ears fascinated with one of my coworkers. I spend a lot of time thinking about her. And it seems that she is, or was, a bit flirtatious with me. Asking her out seemed like a bad idea, as my girlfriend and her husband probably would not have been cool with it. But we’ve dispensed with those losers. So anyway, last week I completed my latest painting. I e-mailed an image of it to various coworkers who are fans of my stuff. It was universally acclaimed by every one of them. I rather like it myself, and wonder if it couldn’t fetch $250 in a gallery. The lovely lady in question especially gushed over it. So I was thinking – good idea to frame it and give it to her? Or would I just come off looking like a desparate fool that can’t get a date outside of my own office? Or should I just man up and ask her out already? [/QUOTE] I need to see the picture first. ---
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 5:41pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/4 "2007-03-19T17:41:28Z")
[QUOTE=Kalhoun] I need to see the picture first. [/QUOTE] [OK.](http://home.comcast.net/~nealtodd/000_0394.jpg) ---
**Author:** ![Frylock](https://avatars.discourse-cdn.com/v4/letter/f/ce7236/32.png) [@Frylock](https://boards.straightdope.com/u/Frylock)\ **Post date:** [March 19, 2007, 5:46pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/5 "2007-03-19T17:46:25Z")
Does she really like the picture, or is it that she likes you? If the latter, then giving her the picture is not ideal. It maintains a distance she was hoping would collapse. It keeps the focus of the relationship on the picture, rather than on the two of you. If the former, then its still not a great idea to give her the picture. For one thing, perhaps she likes the picture but doesn’t like you “that way.” Then the giving of the picture might seem to create inappropriate obligations of various kinds, and this can be awkward and stupid. On the other hand, maybe she likes the picture and she likes you “that way” as well. Then a better strategy is to start with coffee, and so on, and later, create a work _especially_ for her and give it on an anniversary or something. On the other hand, I don’t know you or her personally, and it may be that between the two of you, giant unjustified romantic gestures are just exactly the way to procede. I can imagine such a couple. So aren’t I a lot of help? -FrL- ---
**Author:** ![Phlosphr](https://avatars.discourse-cdn.com/v4/letter/p/c68b51/32.png) [@Phlosphr](https://boards.straightdope.com/u/Phlosphr)\ **Post date:** [March 19, 2007, 5:47pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/6 "2007-03-19T17:47:00Z")
Husband? Were you kidding about that part? Nice painting. What kind of bird is that? ---
**Author:** ![Giraffe](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/giraffe/32/129_2.png) [@Giraffe](https://boards.straightdope.com/u/Giraffe)\ **Post date:** [March 19, 2007, 5:50pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/7 "2007-03-19T17:50:05Z")
Ask her out first. In nearly all cases, it’s better not to make a big production out of liking someone before you ask them out. It’s just too easy to come across as needy and obsessive. If you guys go out a few times and seem to be hitting it off, give her the painting. You’ll then look thoughtful and romantic, at which point she’ll almost certainly chew through your underpants. ---
**Author:** ![Grossbottom](https://avatars.discourse-cdn.com/v4/letter/g/ba8739/32.png) [@Grossbottom](https://boards.straightdope.com/u/Grossbottom)\ **Post date:** [March 19, 2007, 6:01pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/8 "2007-03-19T18:01:27Z")
I think it seems loserish, especially since if you hold back then when you finally do give her a painting, it’ll be like…A Moment. But if you do decide to do it, don’t frame it. Good frames are expensive. Put it in a crappy frame, she’ll think you’re cheap or poor. Put in a good frame, and you’re trying too hard. Just give her the canvas and let her decide, and try to be as unassuming and yet confident as possible when doing something like this. And don’t stand around afterwards with this wistful, horny look on your face, like you’re expecting a quid pro quo mercy fuck. Just be cool and roll on, because the ball will definitely be in her court. ---
**Author:** ![burundi](https://avatars.discourse-cdn.com/v4/letter/b/3ec8ea/32.png) [@burundi](https://boards.straightdope.com/u/burundi)\ **Post date:** [March 19, 2007, 6:03pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/9 "2007-03-19T18:03:26Z")
That’s quite a gift to give a co-worker. It would make me uncomfortable. I think you have a better chance of starting a relationship if you ask her out instead of giving her the painting. ---
**Author:** ![Kalhoun](https://avatars.discourse-cdn.com/v4/letter/k/3bc359/32.png) [@Kalhoun](https://boards.straightdope.com/u/Kalhoun)\ **Post date:** [March 19, 2007, 6:12pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/10 "2007-03-19T18:12:57Z")
Very nice picture. I particularly like the warm colors on the (boardwalk?) area. That said, don’t give it to her. It’s too much, too personal, and too risky. Ask her out. When you two get married, you can display the painting proudly in your foyer. ---
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 6:22pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/11 "2007-03-19T18:22:50Z")
[QUOTE=Phlosphr] Husband? Were you kidding about that part? [/QUOTE] They split about a year and a half ago. I tend to agree that it would be creepy. What would concern me most is if it turns out that she’s now seeing someone, then I would feel like a real tool. (She hasn’t mentioned seeing anyone, but she doesn’t really share her personal life.) I think I need to just approach the situation in the normal way. If only I could work up the nerve! Having said that, not only did I give a painting to another coworker, but I painted it specifically for her. She saw an earlier version (also given away to yet another coworker, but as part of a gift exchange), and absolutely gushed over it. There was no weirdness at all about it, in fact it drew us a little closer. Of course, that was in late December, so unbidden gift giving wouldn’t have seemed so strange. ---
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 6:24pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/12 "2007-03-19T18:24:29Z")
[QUOTE=Kalhoun] Very nice picture. I particularly like the warm colors on the (boardwalk?) area. [/QUOTE] Thanks! > [@](#): > > Ask her out. **When you two get married** , you can display the painting proudly in your foyer. Good plan. The part I bolded is my favorite. 🙂 ---
**Author:** ![Phlosphr](https://avatars.discourse-cdn.com/v4/letter/p/c68b51/32.png) [@Phlosphr](https://boards.straightdope.com/u/Phlosphr)\ **Post date:** [March 19, 2007, 6:33pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/13 "2007-03-19T18:33:23Z")
[QUOTE=tdn] I tend to agree that it would be creepy. What would concern me most is if it turns out that she’s now seeing someone, then I would feel like a real tool. (She hasn’t mentioned seeing anyone, but she doesn’t really share her personal life.) [/QUOTE] Just think - you walk up, ask her out, and then…then…then…it’s over. She answers yes or no… You’ll be fine. The worse case scenerio would be if she completely misconstrues how you ask her out and gets all bent out of shape - think corporate sexual harrassment - but I don’t see that happening. She will do one of two things: 1 - feel flattered and say no, sorry, and blush a little while she tells you the reason why not. Or 2 - feel flattered and say “…sure Todd, where would you like to go? Dinner? Lunch? …” Either way it’s 45 seconds of weirdness. You’ll be fine. ---
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 7:14pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/14 "2007-03-19T19:14:29Z")
[QUOTE=Phlosphr] Just think - you walk up, ask her out, and then…then…then…it’s over. She answers yes or no… You’ll be fine. [/QUOTE] Yes, you’re right. The problem is getting her alone to ask her. She shares an office with two other people. I really don’t want an audience for my Big Rejection. ---
**Author:** ![Phlosphr](https://avatars.discourse-cdn.com/v4/letter/p/c68b51/32.png) [@Phlosphr](https://boards.straightdope.com/u/Phlosphr)\ **Post date:** [March 19, 2007, 7:18pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/15 "2007-03-19T19:18:28Z")
[QUOTE=tdn] Yes, you’re right. The problem is getting her alone to ask her. She shares an office with two other people. I really don’t want an audience for my Big Rejection. [/QUOTE] Does she have a vehicle she must walk out to every evening? Or would that be too creepy? ---
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 7:21pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/16 "2007-03-19T19:21:12Z")
[QUOTE=Phlosphr] Does she have a vehicle she must walk out to every evening? Or would that be too creepy? [/QUOTE] She takes the train, and she leaves a good two hours before I do. ---
**Author:** ![Cat\_Whisperer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cat_whisperer/32/4839_2.png) [@Cat\_Whisperer](https://boards.straightdope.com/u/Cat_Whisperer)\ **Post date:** [March 19, 2007, 7:29pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/17 "2007-03-19T19:29:58Z")
You work together - do you ever have lunch together? If you ask her out, it’s better to do it sooner than later - just rip that bandaid off, man. You could ask her out to lunch as a quasi-date, and then ask her for a proper date at that lunch. And your painting is lovely. Do you ever paint cougars? I got my husband a limited edition print of [Robert Bateman’s “Excursion”](http://www.galleryone.com/images/bateman/bateman_-_excursion_-_cougar_and_kits.JPG) for his engagement present. We got it framed for a present to ourselves later that year. (It’s a truly beautiful painting - the link doesn’t really do it justice.) ---
**Author:** ![Phlosphr](https://avatars.discourse-cdn.com/v4/letter/p/c68b51/32.png) [@Phlosphr](https://boards.straightdope.com/u/Phlosphr)\ **Post date:** [March 19, 2007, 7:30pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/18 "2007-03-19T19:30:00Z")
[QUOTE=tdn] She takes the train, and she leaves a good two hours before I do. [/QUOTE] Perhaps following her down the elevator or stairs…Or “…I didn’t know you took this train…” while you both get on the same train… ---
**Author:** ![tdn](https://avatars.discourse-cdn.com/v4/letter/t/94ad74/32.png) [@tdn](https://boards.straightdope.com/u/tdn)\ **Post date:** [March 19, 2007, 7:42pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/19 "2007-03-19T19:42:08Z")
[QUOTE=featherlou] You work together - do you ever have lunch together? If you ask her out, it’s better to do it sooner than later - just rip that bandaid off, man. You could ask her out to lunch as a quasi-date, and then ask her for a proper date at that lunch. [/QUOTE] That’s an idea. Too bad there aren’t any real restaurants in this neighborhood. Well, there’s one, but it looks more like a bar that a restaurant. > [@](#): > > And your painting is lovely. Do you ever paint cougars? Thank you! I don’t do animals. Except seagulls. And little girls. In fact, a painting with one of each is the one I did twice to give away twice. It’s a people pleaser. I could probably make a nice living doing that one over and over again, but a) I’d have to kill myself, and b) I’m afraid it would become the next Dogs Playing Poker. ---
**Author:** ![NurseCarmen](https://avatars.discourse-cdn.com/v4/letter/n/5daacb/32.png) [@NurseCarmen](https://boards.straightdope.com/u/NurseCarmen)\ **Post date:** [March 19, 2007, 7:42pm UTC](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588/20 "2007-03-19T19:42:31Z")
Creepy would be if it was a painting of her naked, only with much bigger boobies. That’s a nice painting, and I wouldn’t think it creepy at all. [Next page](https://boards.straightdope.com/t/romantic-stupid-or-just-creepy-you-decide/396588.md?page=2)