How Do I Tell Her That I Like Her?

75and10 asks:

I recently got the courage to ask out a girl I’ve been friends with for a long time out to coffee. We went there and talked for two hours and everything was just grand. This last week her and I went bowling together just the two of us and now we’re going rollerblading together in a couple of days. This all sounds awesome right? Well it is but I haven’t told her directly how I feel about her, nor has she told me how she feels about me so everything is up in the air as we have been friends for over 3 years. For all I know she could consider this just friendly hanging out. How can I make it clear how I feel on this upcoming rollerblading “date” how I feel? Should I just tell her directly?

Well good on you for taking the initiative and asking this girl out. It sounds like you clearly like her, so making steps toward getting her out on one-on-one activities was a huge step in the right direction. How you proceed next is up to you but here’s what I would do.

The first thing I would do is ask her on a date that was a bit more focused on conversations. So far you’ve done a coffee date, bowling, and rollerblading. All great choices, but you need a date that has a main focus where you talk. Sure, a coffee date is fine, but after that first cup of coffee you’re not going to sit somewhere for an hour or two just getting to know her, right? No, you need a nice dinner or bar date to really sit for a long period of time and talk. This sort of date also crosses the line from Friendly activity into romantic activity. A dinner date doesn’t always mean romantic intent, but it’s a bit more romantic than a coffee date.

Once you ask her on one of these date, you need to be clear about your intentions and interest. If you want to date her, you need to either say that very clearly, or tell her that dinner is a date. There are subtle ways to tell someone you’re interested in dating, but I’d avoid them. Just be open about your interest and being more than friends and brace yourself for a potential rejection. More than anything else, remember that rejection is a possibility, but you also might end dating her, so it’s worth the risk.

Good Luck Out There.

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