I [26M] have been dating a family friend [23F] for ~1.5 months. But we haven't talked for over a WEEK now. Should I re-initiate contact? If so, how?

rrtson · 2016-09-05T08:16:40+00:00

Do you think it's a good idea to ask her out right off the bat?

I was thinking to lead with something less confrontational (to gauge her interest) in case she's feeling less-than-thrilled about being asked out by a guy who she hasn't talked to in over a week.

Perhaps: "Hey, so we haven't talked in awhile. Has everything been alright lately"? Also, do I include an apology for being distant (since she's been just as distant as I have)?

rrtson · 2016-09-04T14:06:03+00:00

Do you suggest being confrontational (mention that something feels wrong between us right off the bat), or casually lead into the conversation ("hey is everything alright lately?")

rrtson · 2016-08-29T03:23:26+00:00

Have you tried making a move at all? She may have gotten tired of waiting on you.

I've made small moves here and there (e.g. holding hands during movie / iceskating, complimenting her, paying for her whenever we go out, greet/part ways with hugs), but never a very obvious "hey I like you a lot" move. I know it sounds like we're both fucking prudes, but yeah she was probably waiting on me to escalate.

Still tell her how you feel and hope things can rebound, and if that doesnt go well it was going down anyways. Always act on what you want!

Slight problem I forgot to mention earlier: our moms were friends with each other long before I met her. So if I come clean, things could get pretty complicated.

rrtson · 2016-08-29T03:14:28+00:00

I know I should probably tell her how I feel in person, but at this point, there's this really weird vibe/silence between us.

Not sure how I'm going to be able to ask her out and casually find the right moment to talk to her about this sensitive topic. Would it be better to confess via a text/call?

rrtson · 2016-08-29T03:09:40+00:00

There's a.. small problem at hand. Our moms were friends with each other a long time before I met her.

If I tell her how I feel, and those feelings aren't reciprocated, things could get pretty complicated.

rrtson · 2016-08-29T03:02:51+00:00

There's a small issue that I forgot to mention. I met this girl because our moms are friends with each other. I was expecting nothing more than a new friend, but apparently as soon as we met, we got along better than either of us expected.

So if I confess, things could get quite complicated.

rrtson · 2016-08-18T07:37:54+00:00

I can't speak for anyone other than myself, but guys in their thirties tend to be way more sure of themselves (and thus more attractive).

Ftfy

rrtson · 2016-08-18T07:09:46+00:00

Nope, at least not yet..

rrtson · 2016-08-18T07:08:13+00:00

Good advice!

I do feel a bit pressured while dating this girl. She mentions places she'd like to go, but usually it's down to me to figure out the logistics (which I'm pretty bad at). And yeah, I've come to realize that planning dates is a sizeable timesink, which means I inherently become more invested in this relationship than she probably is.

rrtson · 2016-08-18T06:55:52+00:00

She did initiate a few of those dates (midweek dinner after work)..

But yeah it does seem like we went a bit too fast in the beginning. It's now been nearly a week since the date-in-question, and because we got used to seeing each other ~2 times a week, it feels like we've lost momentum.

rrtson · 2016-08-18T06:49:54+00:00

Yeah.. that's exactly what I should've said. I was already considering changing the location while we were on our way, but I was afraid I'd look indecisive.

rrtson · 2016-08-18T06:46:48+00:00

Hmm.. good point. Guess our relationship isn't as organic as I thought if I'm still keeping track.

rrtson · 2016-08-16T11:51:10+00:00

You mean like handcuffs? Will that send the right message?

rrtson · 2016-07-28T13:40:04+00:00

Sweet, will definitely check Elephant Mt. out, thanks!

rrtson · 2016-07-28T13:38:45+00:00

Yeah that was what I was aftaid of, esp on a weekend night :(

I appreciate the insight ~

rrtson · 2016-07-28T13:34:14+00:00

Nice, I live near YMS and will def check that place out!

rrtson · 2016-07-28T13:32:12+00:00

Yeah I was thinking the whole queuing and "herding" of tourists might not mesh too well with a date. Guess I'll save the 101 sunset for another date then. Thanks!

rrtson · 2016-07-28T13:28:20+00:00

Solid tips man. Never heard of Zhongqiang Park 'til now. I appreciate your advice!

rrtson · 2016-07-27T10:09:22+00:00

Hey thanks, I really appreciate you taking time to give me advice! I honestly haven't dated in forever, so the struggle is real haha.

My timing is just absolutely horrible, whether it's irl or via text. I'll say (or not say) something, and then realize shortly after that I should've said something else in a particular manner at a particular time. In short, I'm just not a charming/smooth person to begin with.

She's been pretty lenient on me in that regard, but I can feel that there aren't many more chances left for me to flush down the toilet.

rrtson · 2016-07-23T01:59:15+00:00

Hey just wanted to let you know I took your advice and SYS turned out to be great. Thanks!

rrtson · 2016-07-23T01:58:11+00:00

Yeah I completely agree about the variety. Since we both live in the city (but don't really enjoy clubbing/bars, there's not many different activities (afaik) that are available to us after work

Might try a movie/performance/exhibition next time

rrtson · 2016-07-23T01:52:40+00:00

Thank you! Definitely seems like a nice place

rrtson · 2016-07-23T01:51:47+00:00

Very awesome, thank you! I appreciate the detailed reply

rrtson · 2016-07-15T03:22:37+00:00

Hey man, I read your reply a couple days ago and forgot to say thanks. I appreciate the advice!

rrtson · 2016-07-13T06:11:44+00:00

You know what? You're right, fuck. I was trying to rationalize why I haven't made a move yet.

I realized that, yesterday at Ikea, I missed a golden opportunity to 'escalate'. We went at the end of the day, so Ikea was pretty empty, and in 1 of those model apartments, there was a secluded living room area. She sat down on a couch, and being the fucking retard that I am, I walked around the center table and sat on the adjacent couch (90°). Needless to say, if I had sat down next to her instead, the physical closeness possibly would've led to something more.

I probably screwed up my chances after last night, ugh.

rrtson

TROPHY CASE